Thionyl Chloride → 2-((2-Chloro-6-fluorophenyl)amino)-N-(4-cyclopropylphenyl)-1,7,7-trimethyl-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)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic acid (Intermediate-49, 0.100 g, 0.256 mmol), thionyl chloride (2.0 mL), 4-cyclopropyl aniline (0.102 g, 0.769 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.017 g of the desired product. 1HNMR (DMSO-d6): δ 0.62 (d, J=3.9 Hz, 2H), 0.91 (d, J=6.3 Hz, 2H), 1.60 (s, 6H), 1.88 (m, 1H), 3.45 (s, 2H), 3.55 (s, 3H), 6.98-7.16 (m, 3H), 7.19-7.36 (m, 3H), 7.53 (d, J=8.1 Hz, 2H), 9.60 (s, 1H), 10.48 (s, 1H); MS [M+H]+: 505.26.

Provenance & Evidence