Dimethylformamide → N1-(2-(6-(3-(trifluoromethyl)benzylamino)pyrimidin-4-yl)-4-chlorophenyl)-N3-(2-(2-hydroxyethoxy)ethyl)isophthalamide

Participants

Reaction Conditions

Reaction Steps

Into a 50-mL round bottom flask, was placed a solution of N-(3-(trifluoromethyl)benzyl)-6-(2-amino-5-chlorophenyl)pyrimidin-4-amine (200 mg, 0.53 mmol, 1.00 equiv) in N,N-dimethylformamide (20 mL), HATU (290 mg, 0.76 mmol, 2.00 equiv), N,N-diisopropylethylamine (200 mg, 1.55 mmol, 4.00 equiv), and N1-(2-(6-(3-(trifluoromethyl)benzylamino)pyrimidin-4-yl)-4-chlorophenyl)-N3 hydroxyethoxy)ethyl)isophthalamide (60 mg, 0.10 mmol, 1.50 equiv). The resulting solution was stirred overnight at 30° C. in an oil bath. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The crude product was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 105.9 mg (33%) of a yellow solid. 1H-NMR (300 MHz, DMSO-d6, ppm): δ 8.87 (s, 1H), 8.71 (t, J=4.8 Hz, 9.9 Hz, 1H), 8.49 (s, 1H), 8.07 (t, J=7.5 Hz, 15.3 Hz, 2H), 7.83 (s, 1H), 7.58 (m, 6H), 7.07 (s, 1H), 4.75 (s, 2H), 3.57 (m, 2H), 3.49 (m, 6H). MS (ES, m/z): 614 [M+H]+.

Provenance & Evidence