Category: 294-90-6

294-90-6, 1,4,7,10-Tetraazacyclododecane is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the three-necked flask was added 1,4,7,10-tetraazacyclododecane (100 g, 0.58 mol)10 ml of deionized water, stirred, 30% KOH solution was added dropwise,The pH was adjusted to 8.5 and then chloroacetic acid (263 g, 2.78 mol) was added,And then 30% KOH solution to adjust the pH to 8.5,Heated to 80 C for 24 h, during which the pH was maintained between 8.5 and 9.After the reaction, cooling, adding concentrated hydrochloric acid to adjust the pH to 2, a white precipitate produced, filtered. The filter cake was recrystallized from a water-ethanol solution and the resulting crystals were washed with ethanol, ether, dried,183 g of DOTA crystals was obtained in a yield of 78%.

294-90-6, The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; Wang Jianping; Wang Jianguo; (23 pag.)CN104447598; (2017); B;,
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.294-90-6,1,4,7,10-Tetraazacyclododecane,as a common compound, the synthetic route is as follows.

To a suspension of cyclen (500 g, 29 rnrnol) and sodium acetate (7.86 g, 96 mrnol) in N,N-dirnethylacetarnide (DMA, 60 rnL) at 2O C was added a solution of t-butyl bromoacetate (18.7 g, 14.1 mL, 96 mmol) in DMA (20 rnL) dropwise over a period of 0.5 h. The temperature was maintained at -20 C during the addition, after which the reaction mixture was allowed to come to room temperature. After 24 h of vigorous stirring, thereaction mixture was poured into water (300 rnL) to give a clear solution. Solid KHCO3 (15 g, 150 rnrnol) was added portion wise, and 4 precipitated as a white solid. The precipitate was collected by filtration and dissolved in CHCI3 (250 mL). The solution was washed with water (100 mL), dried (MgSO4), filtered, and concentrated to about 2O3O tnL. Ether (250 mE) was added, after which HHY-330 crystallized as a white fluffy solid.Yield: 12.5 g (73%). ESI-MS found: [M+Ht = 515.5 (Moore, D. A. Org. Synth. 2008, 85,1O-14).

294-90-6, The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SANOFI; EUROPEAN MOLECULAR BIOLOGY LABORATORY; HU, Hai-Yu; NAZARE, Marc; HAN LIM, Ngee; DING-PFENNIGDORFF, Danping; PLETTENBURG, Oliver; RITZELER, olaf; JURETSCHKE, Hans-Paul; SAAS, Joachim; BARTNIK, Eckart; FLORIAN, Peter; WENDT, Ulrich; SCHULTZ, Carsten; NAGASE, Hideaki; WO2015/75699; (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.294-90-6,1,4,7,10-Tetraazacyclododecane,as a common compound, the synthetic route is as follows.

To a solution of cyclen (S4, 1.73 g, 10.0 mmol) and triethylamine (4.20 mL, 30.1 mmol)in CHCI3 (120 mL, freshly passed through A1203 (activated, neutral, Brockmann I)) at 0C was added dropwise a solution of di-tert-butyl dicarbonate (6.55 g, 30.0 mmol) inCHCl (100 mL, freshly passed through A1203 (activated, neutral, Brockmann I)) under N2. After the addition was complete, the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, EtOAc:hexane = 3:2 ramping to EtOAc) to give S6 as a white foam (3.41 g, 72%).RF (EtOAc:hexane = 4:1) 0.63. IR vmax/cm1 3313, 2974, 2931, 2818, 1679, 1463, 1412,365, 1313, 1247, 1156, 1 046, 771, 736. 1H NMR (400 MHz, CDCI3) 5 1.45 (5, 1 8H, 2 x C(CH3)3), 1.47 (5, 9H, C(CH3)3), 2.78-2.92 (m, 4H, CH2NHCH2), 3.16-3.34 (m, 6H),3.34-3.50 (m, 2H), 3.55-3.75 (m, 4H) (total 12H, 3 x CH2N(Boc)CH2) (one secondary amine proton signal (NH) not observed). ?3C NMR (100 MHz, CDCI3) 5 28.1, 28.2, 28.3,28.4, 28.5, 44.7, 45.7, 48.8, 49.2, 50.3, 50.8, 78.9, 79.1, 155.1, 155.4 (eight carbon signals overlapping or obscured). MS (ESI) m/z 472.9 ([M+H], 27%), 495.0 ([M+Na], 99%), 967.1 ([2M+Na], 100%). The spectroscopic data were in agreement with those in the literature.3739, 294-90-6

294-90-6 1,4,7,10-Tetraazacyclododecane 64963, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; THE UNIVERSITY OF SYDNEY; RUTLEDGE, Peter; TODD, Matthew; TRICCAS, James Anthony; WO2014/153624; (2014); 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.294-90-6,1,4,7,10-Tetraazacyclododecane,as a common compound, the synthetic route is as follows.

1-(N-acetyl-aza-15-crown-5)-1,4,7,10-tetraazacyclododecane (1b). 260.0 mg (0.88 mmol) 1a dissolved in 10 mL anhyrous acetonitrile was added dropwise to a mixture of cyclen (378.5 mg, 2.20 mmol, 2.5 equiv.), potassium carbonate (5.0 equivs) in 40 mL warm anhydrous acetonitrile under N2 atmosphere for approximately half an hour. The mixture was then stirred at 65-70 C. for about 12 h. The solution was filtered under reduced pressure and the filtrate was evaporated to leave a crude oil that was purified by column chromatography on aluminium oxide with DCM_MeOH=100:5 as an eluent. The product 2 was isolated as a colorless oil (326.6 mg, 0.76 mmol, 86%). 1H NMR (400 MHz, CDCl3): delta 3.74-3.66 (2H, t, J=6.2 Hz), 3.59-3.47 (14H, m), 3.46-3.36 (6H, m), 2.95-2.93 (1H, br), 2.84-2.81 (1H, br), 2.79-2.70 (7H, m), 2.62-2.54 (7H, m); 13C NMR (100 MHz, CDCl3): delta 171.3 (C), 71.4 (CH2), 70.5 (CH2), 70.2 (CH2), 69.9 (3¡ÁCH2), 69.7 (CH2), 69.3 (CH2), 56.9 (CH2), 56.0 (CH2), 52.3 (CH2), 52.1 (CH2), 49.6 (CH2), 49.4 (CH2), 48.5 (CH2), 48.0 (CH2), 46.7 (CH2), 45.6 (CH2), 45.3 (CH2); ESI-MS m/z 432.4 (M+H)+; HRFAB-MS m/z 432.3193 (M+H)+[Calcd. for C20H42N5O5 (M+H)+, 432.3186].

294-90-6, The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wong, Wing-Tak; Li, Cong; US2006/57071; (2006); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

294-90-6, 1,4,7,10-Tetraazacyclododecane is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,294-90-6

To a 100 mL round bottom flask fitted with a reflux condenser and stir bar was added 1.4696 g Cyclen (8.5 mmol). 5.44 11 g of 2-bromoacetamide (39.4 mmol, 4.6 eq) was added with 4.5748 g triethylamine (44.9 mmol, 5.3 eq) in 30 mL absolute ethanol. The contents were refluxed for 4 hours at 80 C, after which time a white precipitate formed in the flask. After cooling to room temperature, the precipitate was decanted and placed in a 250 mL round bottom flask, then dissolved in 200 mL of hot 80 % ethanol/20 % water. The volume was reduced by approximately 30 % on a roto-evaporator, then placed in the refrigerator overnight to produce white crystals. The remaining solvent was removed by filtration and the crystals were transferred to a 50 mL round bottom flask to dry on a Schlenk line under vacuum for several hours (66 % yield). ESI-MS: m/z = 401.3 (100 %), 402.3 (15 %) [M + H]+; 423.4 (25 %), 424.4 (< 10 %) [M + Na]+. 1H NMR (500 MHz, D20), ppm: 3.02 (s, amide pendent CH28H), 2.57 (s, Cyclen ring 16 H). 13C NMR (125 MHz, D20), ppm: 174.07 (carbonyl C),55.86 (amide CH2), 50.42 (ring CH2). As the paragraph descriping shows that 294-90-6 is playing an increasingly important role. Reference£º
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK UNIVERSITY AT BUFFALO; HEALTH RESEARCH, INC.; MORROW, Janet, R.; TSITOVICH, Pavel, B.; DORAZIO, Sarina, J.; OLATUNDE, Abiola, O.; SNYDER, Eric, M.; SPERNYAK, Joseph, A.; BURNS, Patrick; BOND, Christopher, J.; WO2015/38943; (2015); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

294-90-6, 1,4,7,10-Tetraazacyclododecane is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-(tert-Butoxycarbonyloxy)succinimide (2.50 g, 11.62 mmol) inchloroform (30 mL) was added dropwise into the solution of1,4,7,10-tetraazacyclododecane (1.00 g, 5.80 mmol) in CHCl3(50 mL) during 7 h. The reaction mixture was stirred 24 h at roomtemperature and the solvent was removed under reduced pressure. The residue was suspended in aqueous NaOH (3 M, 50 mL) and theaqueous phase was extracted with CHCl3 (3 50 mL). The combinedextracts were dried with K2CO3 and evaporated to drynessto give 1,7-bis(tert-butoxycarbonyl)-1,4,7,10-tetraazacyclododecane(10) in quantitative yield.1,3,5-Tris(bromomethyl)benzene (7.65 g, 21.62 mmol) was dissolvedin CHCl3 (150 mL) and Na2CO3 (1.71 g, 16.15 mmol) wasadded. Compound 10 (1.08 g, 2.90 mmol) in CHCl3 (50 mL) wasadded dropwise into the reaction mixture during 11 hours at52 C. The reaction mixture was refluxed for 3 days at 62 C,filtrated, and evaporated to dryness. The residue was purified bysilica gel chromatography (40-70% EtOAc in hexane), giving 11 in27% yield (0.722 g). 1H NMR (500 MHz, CDCl3) d 7.33 (s, 6H), 4.45(s, 8H), 3.71 (s, 4H), 3.21-3.57 (m, 8H), 2.55-2.68 (m, 8H), 1.27(s, 18H). 13C NMR (100 MHz, CDCl3) dppm 155.8, 140.8, 138.5,129.9, 128.3, 79.3, 59.5, 55.2, 46.1, 32.9, 28.4. HRMS(ESI): obsd.921.0840 [M+H]+, Calcd. 921.0795 [M+H]+., 294-90-6

The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Laine, Maarit; Loennberg, Tuomas; Helkearo, Mia; Loennberg, Harri; Inorganica Chimica Acta; vol. 452; (2016); p. 111 – 117;,
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.294-90-6,1,4,7,10-Tetraazacyclododecane,as a common compound, the synthetic route is as follows.

Di-tert-butyl dicarbonate (16.5 g, 0.076 mol) in chloroform (100 mL) was added dropwise to a chilled mixture of 1 ,4,7,10-tetraazacyclododecane (5.0 g, 0.029 mol) and diisopropylamine (15 mL, 0.087 mol) in chloroform (200 mL) over a period of three hours. The reaction was then stirred overnight under an atmosphere of nitrogen. The reaction was concentrated, brought up in ethyl acetate (600 mL) and washed with saturated sodium bicarbonate (200 mL), followed by one wash of monobasic potassium phosphate (200 mL of 1 M) and brine (200 mL). The ethyl acetate was dried over sodium sulfate, filtered and concentrated. The crude reaction was purified using flash chromatography (4:1 ethyl acetate :hexanes) to yield a white solid (7.84 g, 57%). 1H NMR (400 MHz, CDCI3) delta 3.67-3.52 (br, 4H), 3.46-3.14 (m, 8H), 2.88-2.72 (br, 4H), 1 .44 (s, 9H), 1 .42 (s, 18H); 13C NMR (100 MHz, CDCI3) delta 155.4, 79.2, 79.1 , 50.8, 49.3, 49.3, 48.7, 45.8, 44.8, 28.5, 28.3; LRMS (ESI): m/z [M+H]+ calc’d for C23H45N406+ 473.33, found 473.33., 294-90-6

The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO; GUNNING, Patrick Thomas; DA SILVA, Sara R.; PAIVA, Stacey-Lynn; LUKKARILA, Julie Lynn; WO2015/179955; (2015); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

294-90-6, 1,4,7,10-Tetraazacyclododecane is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of di-te/t-butyl dicarbonate (6.08 g, 27.8 mmol) in anhydrous CH2CI2 (100 ml) was added dropwise to a stirred solution of cyclen (2.00 g, 11.61 mmol) in anhydrous CH2CI2 (300 ml). The reaction mixture was stirred at room temperature, for 18 h. The solvent was removed under reduced pressure to afford a transparent oil. The crude material was purified by column chromatography on silica (gradient elution: CH2CI2 to 5 % CH3OH : CH2CI2, utilising 0.1 % CH3OH increments) to yield the title compound 17 as a colourless crystalline solid (3.08 g, 6.51 mmol, 56 %); RF = 0.29 (Silica, CH2CI2 – CH3OH, 9 : 1, v/v); 1H NMR (CDCI3, 500 MHz) delta 1.42 (18H, s, feoc CH3), 1.44 (9H, s, *Boc CH3), 2.81 (4H, br s, cyclen CH2), 3.28 (8H, br s, cyclen CH2), 3.60 (4H, br s, cyclen CH2); 13C NMR (CDCI3, 125 MHz, 1H decoupled 500 MHz) delta 28.9 (6C, ‘Boc CH3), 29.0 (3C, ‘Boc CH3), 46.1 (2C, cyclen CH2), 49.9 (2C, cyclen CH2), 51.2 (4C, cyclen CH2), 79.4 (2C, fex*,)), 79.6 (1C, ^oqq)), 155.8 (2C, feoc C = O), 156.0 (1C, ‘Boc C = O); MS (ES+) m/z 473.3 (100 %, [M + H]+); HRMS (ES+) m/z found 473.3330 [M + H]+ C23H45O6N4 requires 473.3333., 294-90-6

The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CIS BIO INTERNATIONAL; LAMARQUE, Laurent; MONTGOMERY, Craig; PARKER, David; WO2010/84090; (2010); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI