Synthetic Route of 302964-08-5, Adding some certain compound to certain chemical reactions, such as: 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide,molecular formula is C16H13Cl2N5OS, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 302964-08-5.
General Procedure A. To a suspension of thiazole-carboxamide 44 (1.0 eq, prepared as outlined in McIntyre, J A et al., Drugs of the Future, 2006, 31(4): 291) in 1,4-dioxane (10 mL/1 mmol) at rt was added diisopropylethylamine (DIPEA, 5.0 eq) followed by the piperazine 45-d4 (1.5 eq to 5.0 eq; generally 1.5 eq of the piperazine analogue was enough to achieve the complete displacement with extended reaction time). The reaction mixture was stirred under reflux conditions until no starting material was detectable (24-72 h), was stripped of solvent in vacuo, then dry-loaded onto a silica-gel column with 94:5:1 CH2Cl2/MeOH/ammonium hydroxide as eluent to give the desired product in 96 to >99% purity. Occasionally, residual solvents, detected by 1H-NMR, were removed by co-evaporation with water. Compound 100: 1H-NMR (300 MHz, DMSO-d6): delta 2.24 (s, 3H), 2.41 (s, 3H), 2.48-2.51 (m, 4H, obscured by DMSO peak), 3.51 (bs, 4H), 4.42 (s, 1H), 6.05 (s, 1H), 7.23-7.31 (m, 2H), 7.41 (dd, J1=7.3, J2=2.0, 1H), 8.22 (s, 1H), 9.90 (s, 1H), 11.50 (s, 1H). 13C-NMR (75 MHz, DMSO-d6): delta 18.20, 25.49, 43.48, 52.57, 82.48, 125.57, 126.92, 128.08, 128.94, 132.32, 133.40, 138.71, 140.71, 156.80, 159.80, 162.26, 162.44, 165.05. HPLC (method: 20 mm C18-RP column-gradient method 2-95% ACN+0.1% formic acid in 3.3 min with 1.7 min hold at 95% ACN; Wavelength: 254 nm): retention time: 2.57 min. MS (M+H): 492.0. Elemental Analysis (C22H22D4ClN7O2S.0.25H2O): Calculated: C=53.22; H=5.38; Cl=7.14; N=19.75; S=
According to the analysis of related databases, 302964-08-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; CONCERT PHARMACEUTICALS INC.; US2009/149399; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia