Pyridine → HCID 15949952, compound

Participants

Reaction Steps

Oxalyl chloride (0.17 mL, 1.94 mmol) and DMF (1 drop) were added to a solution of 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]benzoic acid (625 mg, 1.56 mmol) in DCM (15 mL) and the mixture stirred at RT for 4 hours. The solvent was evaporated in vacuo to a residue which was added to a solution of 2-amino-5-methylpyrazine (255 mg, 2.34 mmol) and pyridine (0.64 mL, 7.8 mmol) in DCM (5 mL). The resultant mixture was heated at 60° C. in a microwave reactor for 5 minutes. The mixture was cooled to RT and pressure, the DCM was evaporated in vacuo to a residue which was partitioned between ethyl acetate (50 mL) and 1N citric acid (25 mL). The organic layer was washed with 1N citric acid (25 mL), brine, dried (MgSO4) and evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate, to give the desired compound (352 mg).

Provenance & Evidence