Hydrochloric Acid → HCID 76281462, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(1-cyano-2-cyclopropyl-1-methyl-ethyl)-5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide (example 150a, 300 mg, 817 μmol) in DMF (4 ml) under an argon atmosphere was added ammonium chloride (218 mg, 4.08 mmol), sodium azide (265 mg, 4.08 mmol). The reaction mixture was stirred at 120° C. under microwave radiation for 45 minutes. After cooling, the reaction mixture was poured into a mixture of ice water (12 mL) and ethyl acetate (4 mL). To the bi-phasic mixture was added sodium nitrite (231 mg, 3.35 mmol) (to decompose the excess of sodium azide), followed by a slow addition of a 4M aqueous solution of hydrochloric acid (until pH=2) under ice cooling. The bi-phasic mixture was then stirred at room temperature for 10 minutes, then diluted with more ethyl acetate and poured into a separatory funnel. After extraction the organic phase was collected and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated down to dryness to yield the title compound (239 mg, 71%) as a crude solid which was used without any purification. MS (ESI, m/z): 411.5 (M+H+).

Provenance & Evidence