Trifluoroacetic acid → HCID 178457790, compound

Participants

Reaction Steps

To a solution of 4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(4-methoxybenzyloxy)-1H-benzo[d]imidazol-2-yl)benzamide (232 mg, 0.415 mmol) in DCM was added TFA (0.96 mL, 1.246 mmol), and the mixture was stirred at RT for 90 minutes. Additional TFA (0.96 mL, 1.246 mmol) was added, and the mixture was stirred at RT for 1 hour longer. The mixture was diluted with DCM, washed with 1 N aqueous NaOH, and the water layer back-extracted with DCM. The aqueous layer was adjusted to pH 8, and the pale green solid was collected and rinsed with 2 mL water. The solid was dissolved in ether and washed with brine, dried over Na2SO4, filtered, and evaporated. The title compound was obtained as a white sold (153 mg, 84% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (d, J=8 Hz, 6H) 1.59 (m, 2H) 1.65-1.82 (m, 2H) 2.02-2.19 (m, 2H) 2.46-2.58 (m, 1H) 2.62-2.79 (m, 2H) 3.93-4.07 (m, 1H) 4.70-4.85 (m, 1H) 6.67 (dd, J=8.61, 2.15 Hz, 1H) 7.03 (d, J=2.05 Hz, 1H) 7.14-7.28 (m, 2H) 7.33 (d, J=8.51 Hz, 1H) 7.64 (d, J=7.82 Hz, 1H) 8.16-8.38 (m, 2H) 9.40 (s, 1H) 12.58 (s, 1H). M/Z calc'd for C24H27FN4O3: 438.50. found 439 [M+H].

Provenance & Evidence