Thionyl Chloride → 2-[(2-Chloro-6-fluorophenyl)amino]-N-[6-(cyclopropylmethoxy)pyridin-3-yl]-7,7-dimethyl-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, 0.200 g, 0.533 mmol), thionyl chloride (2.0 mL), 6-(cyclopropylmethoxy)pyridin-3-amine (Intermediate-42, 0.132 g, 0.799 mmol), THF (5.0 mL), DIPEA (2 mL) and benzene (5 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 2.0% MeOH: DCM to afford 0.120 g of the desired product. 1HNMR (DMSO-d6): δ 0.37-0.74 (m, 4H), 1.20 (m, 1H), 1.53 (s, 6H), 3.06 (s, 2H), 3.74 (d, J=6.9 Hz, 2H), 6.40 (d, J=6.6 Hz, 1H), 7.27-7.30 (m, 2H), 7.39-7.41 (m, 2H), 7.50 (d, J=9.6 Hz, 1H), 8.25 (s, 1H), 9.27 (s, 1H), 11.00 (s, 2H); MS [M+H]+: 522.17.

Provenance & Evidence