Reaction Steps
Ethyl 1-(5-chloro-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate. The title compound was prepared by alkylation of ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate and 5-chloro-4-chloromethyl-[1,2,3]thiadiazole in a manner similar to step (a) of example 1. 1H NMR (DMSO-d6) δ: 8.99 (s, 1H), 8.36 (s, 1H), 7.85 (d, 1H, J=3.0 Hz), 6.75 (d, 1H, J=3.0 Hz), 6.04 (s, 2H), 4.32 (q, 2H, J=7.0 Hz), 1.32 (t, 3H, J=7.0 Hz). LCMS (API-ES, M+H+): 323.0. (b) 1-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(5-chloro-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1 using sodium hydroxide as base and anhydrous ethanol as solvent. 1H NMR (DMSO-d6): δ: 9.01 (s, 1H), 8.35 (s, 1H), 7.85 (d, 1H, J=3.0 Hz), 6.75 (d, 1H, J=3.0 Hz), 5.86 (s, 2H), 4.36 (q, 2H, J=6.8 Hz), 1.42 (t, 3H, J=6.8 Hz). LCMS (API-ES, M+H+): 305.0. (c) 1-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(5-ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid and hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) 6; 11.15 (s, 1H), 8.88 (s, 2H), 8.19 (s, 1H), 7.73 (d, 1H, J=3.0 Hz), 6.66 (d, 1H, J=3.0 Hz), 5.81 (s, 2H), 4.32 (q, 2H, J=6.8 Hz), 1.39 (t, 3H, J=6.9 Hz). LCMS (APCI, M+H+): 320.1. HRMS calcd for C13H14N5O3S (M+H) 320.0817, found 320.0823. HPLC: 100% purity.
