Thionyl Chloride → 2-((2-Chloro-6-fluorophenyl)amino)-N-(2-fluoro-4-methylphenyl)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

Participants

Reaction Steps

The title compound was prepared 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, 0.150 g, 0.400 mmol), thionyl chloride (2.0 mL), 2-fluoro-4-methylaniline (0.075 g, 0.600 mmol), THF (5.0 mL) and DIPEA (3 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.100 g of the desired product. 1HNMR (DMSO-d6): δ 1.54 (s, 6H), 2.29 (s, 3H), 3.17 (s, 2H), 7.00 (d, J=8.4 Hz, 1H), 7.16 (d, J=12.3 Hz, 1H), 7.30 (s, 2H), 7.40 (m, 1H), 7.51 (s, 1H), 8.33 (t, J=8.4 Hz, 1H), 10.02 (s, 1H), 11.12 (s, 2H); MS [M+H]+: 483.17.

Provenance & Evidence