Thionyl Chloride → 2-[(2-Chloro-6-fluorophenyl)amino]-7,7-dimethyl-N-[2-methyl-4-(trifluoromethyl)phenyl]-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamide

Participants

Reaction Steps

The title compound was prepared by following the procedure described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.100 g, 0.266 mmol), thionyl chloride (2.0 mL), 2-methyl-4-(trifluoromethyl)aniline (0.070 g, 0.400 mmol), THF (10.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on neutral alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.56 (s, 6H), 2.41 (s, 3H), 3.12 (s, 2H), 7.32-7.39 (m, 3H), 7.57 (d, J=7.2 Hz, 1H), 7.63 (s, 1H), 8.63 (d, J=8.4 Hz, 2H), 9.31 (s, 1H), 9.84 (s, 1H), 11.18 (s, 1H); MS [M−H]−: 531.41.

Provenance & Evidence