Hydrochloric Acid → HCID 71281044, compound

Participants

Reaction Steps

To a vial was added tert-butyl 3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F39) (145 mg, 0.3 mmol) and 4N HCl in 1,4-dioxane (2 mL) and CH3CN (1 mL). The reaction was stirred for 45 minutes. The solvent was concentrated and placed under high vacuum. The solid was taken in water/acetonitrile and the pH was adjusted to neutral with an aqueous solution of ammonium carbonate and lyophilized to afford N-(5-(5-(azetidin-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (21) which was used directly in the next step. 1H NMR (400 MHz, d6-DMSO) δ 10.85 (s, 1H), 9.66-9.64 (m, 1H), 9.42 (bs, 1H), 9.28 (s, 1H), 8.10-8.08 (m, 2H), 8.02-7.98 (m, 1H), 7.89-7.87 (m, 1H), 7.59-7.53 (m, 2H), 4.53-4.47 (m, 1H), 4.36-4.29 (m, 4H), 2.40 (s, 3H). MS m/z 375.1 (M+1)+.

Provenance & Evidence