Dimethylformamide → Trifluoroacetic acid

Participants

Reaction Steps

N,N-diisopropylamine (99 μL, 0.57 mmol), 3-aminopropane-1,2-diol (35 mg, 0.38 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (130 mg, 0.29 mmol) were added to a solution of 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-3-carboxylic acid (71 mg, 0.19 mmol) in DMF (0.6 mL) and the reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with water and extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC to afford N-(2,3-dihydroxypropyl)-5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-3-carboxamide as a TFA salt. MS ESI calc'd for C21H21F3N5O3 [M+H]+ 448. found 448. 1H NMR (500 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.97 (s, 1H), 8.93 (s, 1H), 8.89-8.79 (m, 1H), 8.78-8.68 (m, 1H), 8.46-8.34 (m, 1H), 8.04-7.93 (m, 1H), 7.60 (s, 1H), 7.32-7.22 (m, 2H), 3.69-3.63 (m, 1H), 3.48-3.39 (m, 2H), 3.25-3.17 (m, 2H), 2.66-2.58 (m, 1H), 2.38 (s, 3H), 2.37-2.32 (m, 1H).

Provenance & Evidence