Thionyl Chloride → HCID 178425066, compound

Participants

Reaction Steps

The title compound was prepared by following the same procedure described for Example-108 by using 2-[(2-Chloro-6-methylphenyl)amino]-7,7-dimethyl-7,8 dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-35, 0.200 g, 0.536 mmol), 2-amino-5-chloro-3-fluoropyridine 1-oxide (Intermediate-43, 0.104 g, 0.643 mmol), thionyl chloride (2 mL), DIPEA (2 mL), benzene (5.0 mL). To a solution of obtained crude product (0.200 g) in acetic acid (10.0 mL) was added iron powder (0.200 g). The reaction mass was stirred at 80° C. for 2-3 h. Excess of Iron powder was separated. The reaction mass was diluted with water, it was extracted with ethyl acetate. The reaction mass was filtered through celite bed and organic layer was separated, dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography on basic alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.021 g of the desired product. 1HNMR (DMSO-d6): 1HNMR (DMSO-d6): δ 1.52 (s, 6H), 2.23 (s, 3H), 3.10 (s, 2H), 7.23-7.31 (m, 2H), 7.40 (d, J=7.8 Hz, 1H), 7.47 (s, 1H), 8.14 (d, J=9.6 Hz, 1H), 8.33 (s, 1H), 9.07 (br s, 1H), 9.84 (s, 1H), 10.92 (brs, 1H); MS [M+H]+: 500.12.

Provenance & Evidence