1,2-Dichloroethane → Trifluoroacetic acid

Participants

Reaction Steps

Dichloromethane (670 μL), EDC (38 mg, 0.20 mmol), methylsulfonamide (25 mg, 0.27 mmol) and DMAP (1.6 mg, 0.013 mmol) were added to 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxylic acid (50 mg, 0.13) and the reaction was allowed to stir for 16 hours at room temperature. DMF (500 μL) was added to the reaction and stirred overnight at room temperature. The reaction was then diluted with aqueous saturated ammonium chloride and extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (10-100% acetonitrile/water with 0.1% TFA) to afford N-(methylsulfonyl)-5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxamide as a TFA salt. MS ESI calc'd for C19H17F3N5O3S [M+H]+ 452. found 452. 1H NMR (500 MHz, DMSO-d6) δ 10.45-10.28 (m, 1H), 9.05-8.91 (m, 1H), 8.92-8.78 (m, 1H), 8.39-8.25 (m, 1H), 8.25-8.12 (m, 1H), 8.12-8.02 (m, 1H), 7.71-7.57 (m, 1H), 7.44-7.21 (m, 1H), 3.39 (s, 3H), 2.40 (s, 3H).

Provenance & Evidence