Water → 4-chloro-3-cyano-5-methyl-N-[(3S,4R)-3-propoxypiperidin-4-yl]-1H-pyrrole-2-carboxamide

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Reaction Steps

A solution of ethyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidine-1-carboxylate (Intermediate 75, 2.6 g, 6.56 mmol), potassium hydroxide (3.67 g, 65.6. mmol), and hydrazine hydrate (3.28 g, 65.6 mmol) in ethylene glycol (100 mL) was stirred for 60 h at 120° C. The reaction mixture was cooled to room temperature and poured into water (75 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried over anhydrous sodium sulphate, filtered, concentrated under vacuum to afford 4-chloro-3-cyano-5-methyl-N-[(3S,4R)-3-propoxypiperidin-4-yl]-1H-pyrrole-2-carboxamide 1.5 g, 71% as solid.

Provenance & Evidence