2-Bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide synthesis
- Product Name:2-Bromo-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide
- CAS Number:1009378-44-2
- Molecular formula:C11H10BrN3OS
- Molecular Weight:312.19
Yield:1009378-44-2 96%
Reaction Conditions:
with (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate;N-ethyl-N,N-diisopropylamine in dichloromethane at 20; for 16 h;
Steps:
49.A
To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid (10.0 g, 45.0 mmol) in methylene chloride (200 mL) was added 3-(aminomethyl) pyridine (5.05 mL, 49.5 mmol), benzotriazol-l-y.oxytris(dimethylamino)phosphonium heafluorophosphate (BOP reagent, 21.9 g, 49.5 mmol) and λ^JV-diisopropylethylamine (15.7 mL, 90.1 mmol). The mixture was stirred under nitrogen at room temperature for 16 hr, then diluted with methylene chloride (300 mL), washed with water (300 mL) and brine (2 x 200 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography over silica gel (methylene chloride:methanol, 95:5) to provide 2-bromo- 4-methyl-thiazole-5-carboxylic acid (pyridine-3-ylmethyl)-amide as a yellow solid (13.5g, 96 % yield). MS (M+H)+ = 313; R1= 1 .0. min.
References:
WO2008/24390,2008,A2 Location in patent:Page/Page column 83
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