Trifluoroacetic acid → N-(4-((2-aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

Participants

Reaction Steps

To a solution of tert-butyl 4-(2,5-difluoro-4-(1-(4-fluorophenylcarbamoyl)cyclopropanecarboxamido)phenoxy)pyridin-2-ylcarbamate (1.8 g, 3.3 mmol) in CH2Cl2 (100 mL) was added TFA (5 mL) and the mixture was stirred at room temperature overnight. The reaction mixture was adjusted to pH>7 with saturated NaHCO3 solution and the separated organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give N-(4-((2-aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (1.2 g, yield 82% yield). 1H-NMR (400 MHz, DMSO-d6): δ 10.99 (s, 1H), 9.76 (s, 1H), 8.04 (dd, J=12.4, 7.6 Hz, 1H), 7.79 (d, J=6.0 Hz, 1H), 7.58-7.55 (m, 2H), 7.47 (dd, J=10.8, 7.2 Hz, 1H), 7.16 (t, J=8.8 Hz, 2H), 6.16 (dd, J=6.0, 2.4 Hz, 1H), 6.00 (br s, 2H), 5.81 (d, J=2.0 Hz, 1H), 1.65-1.62 (m, 2H), 1.56-1.53 (m, 2H); MS (ESI): m/z 443.1 [M+H]+.

Provenance & Evidence