ethyl cyclopropanecarboximidate

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2 atmosphere to a cold solution of methyl 7-amino-2-[(2-chloro-6-fluorophenyl)amino]-6-hydroxy-1H-benzimidazole-5-carboxylate (0.400 g, 1.05 mmol) in DCM (25 mL), was added HCl salt of ethyl cyclopropanecarboximidate (Intermediate-57, 0.234 g, 1.57 mmol) at 0° C. The reaction mass was stirred at 0-5° C. for 1 h and at RT for 24 h. The obtained crude was purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH:DCM to afford 0.150 g of the desired product. (DMSO-d6): δ 1.23 (m, 4H), 2.26 (m, 1H), 3.88 (s, 3H), 6.75 (s, 1H), 7.39 (m, 1H), 7.51 (m, 2H), 7.70 (s, 1H), 9.37 (s, 1H), 11.59 (s, 1H); MS [M+H]+: 401.21. The obtained crude was purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2 atmosphere to a cold solution of methyl 7-amino-2-[(2,6-dichlorophenyl)amino]-6-hydroxy-1H-benzimidazole-5-carboxylate (0.400 g, 1.05 mmol) in DCM (25 mL) was added HCl salt of ethyl cyclopropanecarboximidate (Intermediate-57, 0.234 g, 1.57 mmol) at 0° C. The reaction mass was stirred at 0-5° C. for 1 h and at RT for 24 h. The obtained crude was purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH:DCM to afford 0.150 g of the desired product. (DMSO-d6): δ 1.06-1.14 (m, 4H), 3.88 (s, 3H), 2.3 (m, 1H), 7.41 (s, 1H), 7.62 (d, J=7.8 Hz, 2H), 7.69 (s, 1H), 9.47 (s, 1H), 11.55 (s, 1H). The obtained crude was purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH