Sodium Hydroxide → HCID 178424091, compound

Participants

Reaction Steps

A mixture of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-ethynylimidazo[1,2-a]pyridine-3-carboxamide (53) (10 mg, 0.023 mmol), azidomethyl pivalate (3.64 mg, 0.023 mmol), CuSO4(2 μL of 0.5M aqueous solution, 0.001 mmol) and sodium ascorbate (1.4 mg, 0.007 mmol) in tBuOH/H2O (1 mL, 2:1) was stirred at room temperature overnight. Then the reaction mixture was diluted and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated to afford a residue which was dissolved in MeOH (1 mL). Aqueous NaOH (0.6 mL, 1N) was added and the reaction mixture was stirred for 30 minutes. The above mixture was purified by HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (F65). MS m/z 477.1 (M+1)+.

Provenance & Evidence