4-Methylmorpholine → HCID 71288488, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of intermediate A-1 (32 mg, 153 μmol), 2-(imidazo[1,2-a]pyridin-2-yl)ethanamine dihydrochloride (46.7 mg, 199 μmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 64.1 mg, 169 μmol) and N-methylmorpholine (84.3 μL, 767 μmol) in THF (1.5 mL) was heated under nitrogen atmosphere at 70° C. for 16 hr. The reaction mixture was cooled to RT, poured into ethyl acetate (50 mL) and extracted with water (2×15 mL). The organic phase was washed with brine (15 mL) and the aqueous layers were back-extracted with ethyl acetate (1×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using silica gel and a MeOH/ethyl acetate gradient) to give the title compound (18 mg, 51.1 μmol, 33.3%) as colorless solid. MS: M=353.2 (M+H)+

Provenance & Evidence