Category: 62937-45-5

62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62937-45-5, Example 66; 1-f5-4- (2-Methoxv- (1 R)-methvl-ethoxv)-phenyll-4- (6-methoxy-pyridin-3-vl)-4H- f . 2, 41triazol-3-vlmethvlLpyrrolidine- (2R)-carboxylic acid amide; A mixture of the product of preparation 62 (100mg, 0. 26mol), L-prolinamide (44mg, 0. 39mmol) and potassium carbonate (72mg, 0. 51mmol) were stirred in acetonitrile (10mi), for 18 hours at room temperature, and for 6 hours at 45C. The solvent was then evaporated under reduced pressure and the residue was taken up in ethyl acetate and washed with water and brine. The organic phase was dried over sodium sulfate, concentrated in vacuo, and purified by column chromatography on silica gel, eluting with dichloromethane : methanol : 0.88 ammonia, 98: 2: 0.2, to yield the title compound, 24mg. ‘H NMR (CDC13, 400MHz) d : 1.30 (d, 3H), 1.80 (m, 2H), 2.20 (t, 1H), 2.60 (m, 1H), 3. 10 (t, 1H), 3.20 (m, 1H) 3.40 (s, 3H), 3.50 (m, 1H), 3.60 (m, 1H), 3.80 (d, 1H), 3.90 (d, 1H) 4.00 (s, 3H) 4.60 (m, 1H), 5.10 (s, 1H), 6.80 (d, 1H), 6.90 (d, 2H), 7.30 (d, 2H), 7.40 (d, 1H), 8. 10 (s, 1 H). MS APCI+ m/z 467 [MH] +

62937-45-5 D-Prolinamide 447554, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/82866; (2005); A2;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,62937-45-5

C) (2R)-1-((1-(4-(4-methyl-1H-pyrazol-1-yl)pyridin-3-yl)piperidin-4-yl)carbonyl)pyrrolidine-2-carbonitrile (crude crystals) To a suspension of 1-(4-(4-methyl-1H-pyrazol-1-yl)pyridin-3-yl)piperidine-4-carboxylic acid (80 g) and acetonitrile (0.32 L) were added DIPEA (0.21 L), (R)-prolinamide (40 g) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (1.7M ethyl acetate solution, 0.28 L) at 0C. The mixture was stirred at room temperature for 1 hr, to the mixture was added 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (1.7M ethyl acetate solution, 0.35 L), and the mixture was stirred overnight at 70C. To the mixture was added saturated aqueous sodium hydrogen carbonate solution (1600 mL) at 0C, and the mixture was extracted with a mixed solvent of ethyl acetate and THF. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solution was purified by silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure, to the residue was added diisopropyl ether, and the mixture was stirred overnight at room temperature. The solid was collected by filtration, and washed with diisopropyl ether to give the title compound (93 g). 1H NMR (300 MHz, DMSO-d6) 5 1.57-1.82 (4H, m), 1.89-2.30 (7H, m), 2.53-2.83 (3H, m), 2.86-3.06 (2H, m), 3.41-3.58 (1H, m), 3.62-3.75 (1H, m), 4.72 (1H, dd, J = 7.4, 4.0 Hz), 7.53 (1H, d, J = 5.3 Hz), 7.63 (1H, s), 8.31 (1H, d, J = 5.3 Hz), 8.41 (1H, s), 8.43 (1H, s).

62937-45-5 D-Prolinamide 447554, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; KOIKE, Tatsuki; KAJITA, Yuichi; YOSHIKAWA, Masato; IKEDA, Shuhei; KIMURA, Eiji; HASUI, Tomoaki; NISHI, Toshiya; FUKUDA, Hiromi; EP2933247; (2015); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62937-45-5,D-Prolinamide,as a common compound, the synthetic route is as follows.

62937-45-5, A solution of 5-(4-chlorophenyl)-2-{ [l-(4-chloropyridin-3-yl) H-l,2,4-triazol-3-yl]methyl}-4- [(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-l,2,4-triazol-3-one (Example 6A, 150 mg, 300 muiotaetaomicron) in ethanol (600 mu) was treated with D-prolinamide (342 mg, 3.00 mmol) and heated at reflux overnight. The reaction mixture was purified by preparative HPLC (Method 4) affording 137 mg (79 % of th.) of the title compound. LC-MS (Method 2): Rt = 1.03 min; MS (ESIpos): m/z = 578.2 [M+H]+ -NMR (400 MHz, DMSO-d6) delta [ppm]: 8.73 (s, 1H), 8.27-8.00 (m, 2H), 7.80-7.50 (m, 4H), 7.30 (s, 1H), 7.10 (s, 1H), 6.91 (d, 1H), 6.52 (d, 1H), 5.19-4.99 (m, 2H), 4.40-4.20 (br m, 1H), 4.16-3.76 (m, 3H), 2.93-2.66 (m, 2H), 2.11-1.91 (m, 1H), 1.85-1.44 (m, 3H).

The synthetic route of 62937-45-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; WITTWER, Matthias, Beat; LUSTIG, Klemens; TINEL, Hanna; LINDNER, Niels; SCHIRMER, Heiko; (449 pag.)WO2019/81307; (2019); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5,62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A stirred suspension of 2-chloro-N-(1-methyl-1H-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (1b) (100 mg, 0.40 mmol), (S)-pyrrolidin-2-ylmethanol (122 mg, 1.20 mmol) in N-Methyl-2-pyrrolidinone (1 mL) was subjected to microwave irradiation at 150 C for 2 h. The reaction mixture was diluted with ethyl acetate (50 mL), washed with brine (2 x 20 mL), dried, filtered and concentrated in vacuum. The crude residue was purified by combiflash (silica gel, 12 g, eluting with chloroform/CMA-80) to afford (S)-(1-(4-((1-methyl-1H-imidazol-4-yl)amino)furo[3,2-d]pyrimidin-2-yl)pyrrolidin-2-yl)methanol (2a) (43 mg, 34 % yield) as a light yellow solid; NMR (300 MHz, DMSO-i) delta 9.90 (s, 1H, D20 exchangeable), 8.00 (d, J = 2.1 Hz, 1H), 7.44 (s, 1H), 7.42 (d, J = 1.4 Hz, 1H), 6.71 (d, J = 2.1 Hz, 1H), 4.94 (s, 1H, D2O exchangeable), 4.13 (s, 1H), 3.83 – 3.69 (m, 1H), 3.64 (s, 3H), 3.62 – 3.49 (m, 1H), 3.48 – 3.23 (m, 2H), 2.07 – 1.83 (m, 4H); MS (ES+): 315.4 (M+l), 337.5 (M+Na), (ES-): 313.4 (M- 1). HPLC purity: 98.70%.

62937-45-5 D-Prolinamide 447554, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62937-45-5, Example 53(fi)-1 -[5-(4-{(S)-1 -[(S)-6-(2-Hvdroxy-2-methyl-DroDyl)-2-oxo-6-Dhenyl-[1 .3loxazinan-3-yll- ethyl)-phenyl)-pyridin-2-yl1-pyrrolidine-2-carboxylic acid amide; A mixture of 3-{(S)-1 -[4-(6-fluoro-pyridin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl- propyl)-6-phenyl-[1 ,3]oxazinan-2-one (165 mg), potassium carbonate (76 mg), D-prolinamide (125 mg), and dimethyl sulfoxide (2 ml_) was stirred at 100 ‘ overnight. After cooling to room temperature, aqueous NaHC03 solution was added and the resulting mixture was extracted with dichloromethane. The combined extracts were concentrated and the residue was purified by HPLC on reversed phase (water/methanol) to give the title compound. Yield: 85 mg (43% of theory); Mass spectrum (ESI+): m/z = 543 [M+H]+.

The synthetic route of 62937-45-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LEFTHERIS, Katerina; ZHUANG, Linghang; TICE, Colin, M.; SINGH, Suresh, B.; YE, Yuanjie; XU, Zhenrong; HIMMELSBACH, Frank; ECKHARDT, Matthias; WO2011/159760; (2011); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 7: 1-r(3-(6-Methyl-4-r(3.3.3-trifluoro-2-m(4-fluorophenvnsulfonylU1- methylethv?aminolmethyl’y-2-hvdroxypropy?aminol-1/-/-indazol-1-yl)phenv?carbonyl1- D-prolinamide; lambda/,lambda/-Diisopropylethylamine (0.0644mL) and HATU (29.5mg) were added to a solution of 3-(4-{[2-({ethyl[(4-fluorophenyl)sulfonyl]amino}methyl)-3,3,3-trifluoro-2- hydroxypropyl]amino}-6-methyl-1/-/-indazol-1-yl)benzoic acid (45mg, 0.074mmol) in DMF (1.4mL) and the mixture stirred at room temperature under for 10 min. D- Prolinamide (21.1 mg) was then added and the mixture stirred at room temperature overnight. More D-prolinamide was added and the mixture stirred for a further 24 hours and then diluted slightly with methanol and purified by mass directed autopreparation (System B). Product containing fractions were combined and partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The aqueous phase was re-extracted with dichloromethane and the combined organic extracts were washed successively with water and brine, dried through a hydrophobic frit and evaporated to give the title compound (22.2mg). LCMS: tRET = 3.38 min; MH+ = 70519mg of this mixture of diastereomers was resolved by chiral HPLC on a 2 x 25cm Chiralpak AD column eluted with heptane : iso-propanol 1 : 1 with a flow rate of 15 mL/min to provide Example 7-A (diastereomer A, 6.5mg) and Example 7-B (diastereomer B, 7.5mg).Example 7-A (diastereomer A): Analytical chiral HPLC (25 x 0.46 cm Chiralpak AD column, heptane : iso-propanol 1 : 1 eluting at 1 mL/min): tREtau = 8.6 min LCMS: tRET = 3.41 min; MH+ = 705Example 7-B (diastereomer B): Analytical chiral HPLC (25 x 0.46 cm Chiralpak AD column, heptane : iso-propanol 1 : 1 eluting at 1 mL/min): tREtau = 11.6 min LCMS: tRET = 3.59 min; MH+ = 705, 62937-45-5

As the paragraph descriping shows that 62937-45-5 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/50218; (2009); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5,62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of N((5-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-N-phenylethenesulfonamide (0.100 g, 0.255 mmol), D-(-)-Prolinamide (0.058 g, 0.5 10 mmol) and Diisopropylethylamine (0.176 mL, 1.019 mmol) in dichioromethane (5 mL) was stirred at the room temperature for 24 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; methanol / dichloromethane = 5 % to 10 %) to give(R)- 1 -(2-(N-((5-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-N-phen ylsulfamoyl)ethyl)pyrrolidine-2-carboxamide as white solid (0.045 g, 34.9 %).?H NMR(400 MHz, CD3OD): oe 9.17 (dd, 1 H, J= 2.2, 0.8 Hz), 8.43 (dd, 1 H, J=8.3, 2.3 Hz), 7.76 (dd, 1 H, J = 8.2, 0.8 Hz), 7.55 – 7.44 (m, 2 H), 7.46 – 7.35 (m, 1 H),7.40 – 7.19 (m, 3 H), 5.17 (s, 2 H), 3.63 – 3.46 (m, 2 H), 3.32 – 2.76 (m, 3 H), 2.65 (q, 1H, J= 7.3 Hz), 2.45 -2.28 (m, 1 H), 2.30-2.12 (m, 1 H), 1.92- 1.71 (m, 3 H); LRMS(ES) mlz 507.3 (M¡Â+1).

The synthetic route of 62937-45-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62937-45-5,D-Prolinamide,as a common compound, the synthetic route is as follows.

62937-45-5, In these Reference Examples the following method was used, with volumes and amounts as outlined in Table 1.The racemic mandelic acid derivative 3-chloro,5-difluoro-methoxy mandelic acid and (D)- proline amide were added to ethyl acetate saturated in water (8.1% water in ethyl acetate). The mixture was heated to reflux and stirred for 10 minutes at reflux. The thin suspension was cooled to 23C over 13 hours followed by further cooling to 180C over 40 minutes. The suspension was filtered and washed with ethyl acetate (3 x 30 ml) to give the salt. A sample was dissolved in a 1 : 1 mixture of 1 M HCl and ethyl acetate. The organic layer was separated, concentrated to dryness and analysed by chiral HPLC (for suitable methodology, see Reference Example 1 IA). This showed a high degree of purity of the “correct” enantiomer (see Table 1), (R)- 3-chloro,5-difluoro-methoxy mandelic acid.Table 1MA= racemic mandelic acid derivative, 3-chloro,5-difluoro-methoxy mandelic acid.PA= (D)-proline amide.Eq. PA= Amount of equivalents of (D)-proline amide compared to racemic mandelic acid derivative.EtOAc= ethyl acetate, as solution saturated in water.Water/EtOAc (%) = concentration of water in ethyl acetate. mmol MA/ ml water-EtOAc= concentration range of racemic mandelic acid derivative per ml of ethyl acetate and water. EPO e.e. (%) = enantiomeric excess defined as the % mole fraction denoting the enantiomers in a mixture.1) Corrected for purity, i.e. initially 86% pure racemic mandelic acid derivative.; In these Reference Examples the following method was used, with volumes and amounts as outlined in Table 2.The racemic mandelic acid derivative 3-chloro,5-difluoro-methoxy mandelic acid and (D)- proline amide were added to ethyl acetate and the mixture heated to reflux. At reflux, water was added and the mixture was stirred for another 10 minutes at reflux. The thin suspension was allowed to cool to 18C over 3 hours (in Reference Examples 4-8; 4 hours in Reference Example 9). The suspension was filtered and washed with ethyl acetate (3 x 30 ml) to give the salt. The salt was dissolved in a 1 : 1 mixture of 1 M HCl and ethyl acetate. The organic layer was separated, concentrated to dryness and analysed by chiral HPLC (for suitable methodology, see Reference Example 1 IA). This showed a high degree of purity of the “correct” enantiomer (see Table 2), (R)- 3-chloro,5-difluoro-methoxy mandelic acid.To exemplify in more detail, the following scheme was used in Reference Example 6: The racemic mandelic acid derivative 3-chloro,5-difluoro-methoxy mandelic acid (26.18 g, 93.3 mmol, 1 eq, 90% pure according to HPLC) and (D)-proline amide (4.80 g, 42 mmol, 0.45 eq) were added to ethyl acetate (54.5 ml) and the mixture heated to reflux. At reflux, 5.5 ml of water was added and the mixture stirred for another 10 minutes at reflux. The thin suspension was allowed to cool to 18C over 3 hours. The suspension was filtered and washed with ethyl acetate (3 x 30 ml) to give 8.6 g of the salt. A sample was dissolved in a 1:1 mixture of 1 M HCl and ethyl acetate. The organic layer was separated, concentrated to dryness and analysed by chiral HPLC. This showed 98.2% of the “correct” (i?)-enantiomer. From the mother liquor more material crystallised, which was filtered, washed and dried. This gave another 1.6 g of the salt. The free (i?)-mandelic acid was analysed by HPLC (for suitable methodology, see Reference Example HA) and contained 99.0% of the “correct” enantiomer. EPO Table 2MA = racemic mandelic acid derivative 3-chloro,5-difluoro-methoxy mandelic acid.PA = (D)-proline amide.Eq. PA = Amount of equivalents of proline amide compared to racemic mandelic acid derivativeEtOAc = ethyl acetate in ml.Water/EtOAc (%) = concentration of water in ethyl acetate. mmol MA/ ml water-EtOAc = concentration range of racemic mandelic acid derivative per ml of ethyl acetate and water. e.e. (%) = enantiomeric excess defined as the % mole fraction denoting the enantiomers in a mixture.1) Corrected for purity, i.e. initially 85-90% pure racemic mandelic acid derivative.2) The suspension was allowed to cool to 180C over 4 hours.; A solution of the racemic mandelic acid (obtained after the first racemisation) in ethyl o acetate (1.433 kg of a 29.9% (w/w) solution, 0.429 kg racemic mandelic acid, 1.698 mol, 1.00 eq) was filtered and added within 30 minutes to a stirred solution of D-prolinamide (0.095 kg, 0.853 mol, 0.49 eq) in ethyl acetate (0.407 kg, 0.452 L) as well as water (0.153 kg) at 72-75C. After the addition was completed a clear solution was obtained. The mixture was cooled to 58C within 45 min. No crystallisation was observed. The mixture s was cooled further to 0-20C within 2.5 hours. The salt started to precipitate at approximately 55C. After stirring for a further hour at 0-20C, the solid was filtered off and washed twice with a pre-cooled (0-50C) mixture of ethyl acetate/ water = 9:1 (w/w, 2 x EPO 0.20 kg). A wet,…

62937-45-5 D-Prolinamide 447554, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125964; (2006); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62937-45-5,D-Prolinamide,as a common compound, the synthetic route is as follows.

Methyl /so-butyl ketone (MIBK; 3.87 ml/g of mandelic acid) was added to the mandelic acid (1 eq.) at ambient temperature. Stirring was started and the solution was heated to 80C. A solution of D-prolinamide (0.5 eq.) in MIBK (0.43 ml/g of mandelic acid) and water (3 molar equivalent/mandelic acid) was added and crystallisation started soon after. After half an hour additional MIBK (3.87 ml/g of mandelic acid) was added and then a solution of D-prolinamide (0.7 eq.) in MIBK (0.43 ml/g of mandelic acid) and water (3 molar equivalent/mandelic acid). The suspension was stirred at 100C for 22 hours. The suspension was cooled to O0C over 2.25 hours. The substance was isolated by filtration, washed with MIBK and then dried (crude yield 84.9 %). The ee of the crude D-prolinamide salt of the (i?)-enantiomer of the mandelic acid was 94.32%. If the optical purity and the assay of the salt are not satisfactory, a series of slurry wash experiments in a number of solvents has shown that both the optical purity and the assay (physical content purity) can be improved. A slurry wash in acetone, for example, gave the (R)- mandelic acid.D-prolinamide salt with 99.1% ee. The yield including the slurry wash was 81.8%. With 2-butanone (MEK) as solvent for the slurry wash, the (i?)-mandelic acid.D- prolinamide salt was obtained with 96.0% ee in 83.9% yield. Other solvents or solvent mixtures which can be used for the slurry wash are MIBK with 20 % w/w H2O, acetonitrile, and 2- propanol.

As the paragraph descriping shows that 62937-45-5 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125964; (2006); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

62937-45-5, (R)-chloro[(1,2,3,4,5-eta)-pentamethyl-2,4-cyclopentadien-1-y 1](2-pyrrolidinecarboxamidato-kappaN1, kappaN2)iridium(III) (Cp*Ir(Cl-) (R-PA-H+)) To 40 ml of methylene chloride, 1.593 g of a pentamethylcyclopentadienyl iridium(III) chloride dimer ([Cp*IrCl2]2), 502 mg of (R)-prolinamide and 425 mg of triethylamine were successively added, and the mixture was continuously stirred at room temperature overnight. To the reaction mixture, 10 ml of a 20% aqueous sodium chloride solution was added, and the mixture was stirred for about 30 minutes and then left to stand. The resulting layers were separated. The aqueous layer was extracted with 10 ml of methylene chloride, and then the organic layers were combined and washed with 10 ml of a 20% aqueous sodium chloride solution. Further, this aqueous layer was extracted with 10 ml of methylene chloride, and then the organic layers were combined and dried over 10 g of anhydrous sodium sulfate overnight. The desiccant was filtered off and washed with methylene chloride, and then the filtrate was concentrated in vacuo. To the concentrated residue, 20 ml of tetrahydrofuran/diisopropyl ether (1/1) was added, and the mixture was stirred at 35 to 40C for about 1 hour. The precipitate was collected by suction filtration, washed with 10 ml of tetrahydrofuran/diisopropyl ether (1/1), and then dried in vacuo at 40 to 50C for 5 hours to give 1.813 g of (R)-chloro[(1,2,3,4,5-eta)-pentamethyl-2,4-cyclopentadien-1-y 1](2-pyrrolidinecarboxamidato-kappaN1, kappaN2)iridium(III) (Cp*Ir(Cl-)(R-PA-H+)) as a yellow crystalline powder. Melting point: 174.8C Elemental analysis: C15H24ClIrN2O (476.01) calculated value (%) C37.84, H5.08, N5.88, Ir40.4 found value (%) C37.81, H5.07, N5.93, Ir40.7 IR (KBr): 3429, 3282, 1599 cm-1 1H-NMR (200 MHz, CDCl3) : delta 1.60-2.28 (4H, m, 2 * CH2), 1.70 (15H, s, 5Me of Cp*), 2.71-2.93 (1H, m, one of NCH2), 3.41-3.55 (1H, m, one of NCH2), 3.89-4.01 (1H, m, NCH), 4.96 (2H, br, 2 * NH). 13C-NMR (50.3 MHz, CDCl3) : delta 9.1 (5Me of Cp*), 27.1 (CH2), 28.2 (CH2), 54.3 (NCH2), 62.9 (NCH), 84.4 (ArC of Cp*), 183.5 (C=O).

As the paragraph descriping shows that 62937-45-5 is playing an increasingly important role.

Reference£º
Patent; Hamari Chemicals, Ltd.; MAEDA, Sadayuki; SATO, Tatsunori; KAWANO, Yasuhiko; MIYAWAKI, Toshio; EP2733138; (2014); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI