HCID 59568577, compound → HCID 49783902, compound

Participants

Reaction Steps

(S)-tert-Butyl 4-(1-cyano-2-(3′-cyano-4′-fluorobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 22, step (ii), 353 mg) was dissolved in formic acid (2.5 mL) and the reaction mixture stirred at room temperature for 3 h. The reaction mixture was evaporated to dryness, dissolved in methanol (10 mL), re-evaporated to dryness, dissolved in methanol (5.5 mL) and purified on reversed phase HPLC eluting with methanol in 0.1% aqueous TFA on a Water's SunFire column. The material was converted to free base by evaporating the relevant fractions, dissolving the residue in ethyl acetate (20 mL) and washing with saturated sodium bicarbonate solution (20 mL). The sodium bicarbonate solution was re-extracted with ethyl acetate (20 mL). The combined organic extracts were dried and evaporated to afford the titled compound (209 mg).

Provenance & Evidence