Ethyl chloroformate → HCID 178473353, compound

Participants

Reaction Steps

Ethyl chloroformate (0.1 mmol) in anhydrous THF was slowly added to a solution of N4-(1H-benzo[d]imidazol-2-yl)-N5-(2-methyl-4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide (0.10 mmol) and diisopropylethylamine (0.20 mmol) in anhydrous DMA (5 mL) at 0° C. LCMS indicated that the reaction was complete in 5 minutes. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by preparative reverse phase HPLC (ammonium acetate/acetonitrile) to give 3.4 mg of ethyl 4-({4-[({4-[(1H-benzimidazol-2-ylamino)carbonyl]-1H-imidazol-5-yl}carbonyl)amino]-3-methylphenyl}oxy)piperidine-1-carboxylate. 1H-NMR (400 MHz, DMSO-d6): δ 12.19 (s, 1H), 8.13 (s, 1H), 7.48 (m, 2H), 7.11 (m, 2H), 6.96 (s, 1H), 6.88 (dd, 1H), 4.60 (m, 1H), 4.05 (m, 2H), 3.70 (m, 2H), 3.30 (m, 1H), 2.26 (s, 3H), 1.91 (m, 2H), 1.57 (m, 2H), 1.19 (t, 3H). MS (EI): 532.4 (MH+).

Provenance & Evidence