Diisopropylethylamine → 2-methylpropyl 6-(4-{[2-(3-fluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate

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Reaction Steps

A solution of 2-methylpropyl 6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate trifluoroacetic acid salt (0.20 g, 0.53 mmol), 2-(3-fluorophenyl)-4-oxopiperidine-1-carbonyl chloride (reagent preparation 37) (0.13 g, 0.51 mmol) and diisopropylethylamine (3.0 g, 23 mmol) in N,N-dimethylformamide (8 mL) was heated to 65° C. for 18 hours. The resulting mixture was diluted with ethyl acetate (50 mL) and washed with water (2×25 mL) and once with brine (15 mL) then dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (acetone/ethyl acetate, 1:4) to give 2-methylpropyl 6-(4-{[2-(3-fluorophenyl)-4-oxopiperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate (0.19 g, 64% yield). MS (EI) for C35H35FN5O5: 586 (MH+)

Provenance & Evidence