As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO194,mainly used in chemical industry, its synthesis route is as follows.,19771-63-2
To a solution of 3-[3-[[4-[(3-aminopropyl) amino] -5-bromo-2- pyrimidinyl] amino] PHENYL-2, 4-IMIDAZOLIDINEDIONE hydrogen chloride salt (6.9 g, 13.9 mmol), (-)-2-OXO-4-THIAZOLIDINECARBOXYLIC acid (2.5 g, 17 mmol, 1.2 equiv. ) and N,N-diisopropylethylamine (10 mL, 57.4 MMOL, 4.1 equiv. ) in DIMETHYLFORMAMIDE (150 mL) was added 0-(7-AZABENZOTRIAZOL-1-YL)-N, N, N’, N’ tetramethyluronium HEXAFLUOROPHOSPHATE (6.5 g, 17.1 MMOL, 1.2 equiv. ) at 0 C. The resulting solution was warmed to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure to remove dimethylformamide. The crude residue was triturated in water to give a suspension. The suspension was filtered and the filter cake was washed with water and air-dried (ca. 8 g). The solid was purified by HPLC chromatography using acetonitrile/water to afford the title compounds, (4R)-N-[3-[[5-bromo-2-[[3- (2, 5-dioxo-1-imidazolidinyl) phenyl] amino]-4-pyrimidinyl] amino] PROPYL]-2-OXO-4- thiazolidinecarboxamide (2.8 G) and (4R)-N-[3-[[5-bromo-2-[[3-[2,5-dioxo-3-[[(4R)- 2-oxo-4-thiazolidinyl] carbonyl]-1-imidazolidinyl] phenyl] amino]-4- pyrimidinyl] amino] propyl]-2-oxo-4-thiazolidinecarboxamide (72 mg). N-[3-[[5-bromo-2-[[3-(2,5-dioxo-1-imidazolidinyl)phenyl]amino]-4- pyrimidinyl] amino] propyl]-2-oxo-4-thiazolidinecarboxamide :’H NMR (400 MHz, DMSO-d6) : 5/POM = 1.71 (m, 2H), 3.14 (m, 2H), 3.36 (m, 1H), 3.42 (m, 2H), 3.64 (t, 1H), 4.04 (s, 2H), 4.23 (m, 1H), 6.99 (d, 1H), 7.01 (t, 1H), 7.59 (d, 1H), 7.72 (s, 1 H), 7.81 (br s, 1 H), 8.16 (m, 2H), 8.29 (s, 1H), 8.34 (s, 1H), 9.99 (br s, 1 H). (4R)-N-[3-[[5-bromo-2-[[3-[2,5-dioxo-3-[[(4R)-2-oxo-4-thiazolidinyl]carbonyl]- 1-imidazolidinyl] phenyl] amino]-4-pyrimidinyl] amino] propyl]-2-oxo-4- thiazolidinecarboxamide :’H NMR (400 MHz, DMSO-d6) : 6/POM = 1.64 (m, 2H), 3.12 (m, 2H), 3,38 (m, 4H), 3.79 (m, 2H), 4.02 (s, 2H), 5.04 (d, 2H), 5.12 (d, 2H), 6.94 (d, 1 H), 7.34 (t, 1H), 7.56 (d, 1H), 7.69 (s, 1H), 8.08 (s, 1H), 8.18 (s, 1 H), 8.26 (s, 1 H), 8.37 (s, 1 H), 9.79 (br s, 1 H).
With the complex challenges of chemical substances, we look forward to future research findings about (R)-2-Oxothiazolidine-4-carboxylic acid,belong thiazolidine compound
Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/48343; (2004); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com