Dimethylformamide → Cyclohexanecarboxamide

Participants

Reaction Conditions

Reaction Steps

cis-4-Hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (500 mg, 1.05 mmol), ammonium chloride (112 mg, 2.09 mmol), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (795 mg, 2.09 mmol), and diisopropylethylamine (730 μl, 4.18 mmol) were taken-up in dimethylformamide (4.2 mL) under argon. The vessel was sealed and stirred at 65° C. for 4 hours. Upon cooling, the reaction mixture was diluted with water, and the resulting precipitate was collected via filtration. The solids were washed with water and diethyl ether and dried in vacuo overnight to afford cis-4-hydroxy-4-[5-(3-methyl-5-{[4-Orifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxamide (437.6 mg, 0.916 mmol, 88% yield) as a white solid. MS ESI: [M+H]+ m/z 478.1.

Provenance & Evidence