Pyridine → HCID 68277905, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8A (27 mg, 0.053 mmol) and hydroxylamine hydrochloride (4.3 mg, 0.062 mmol) in pyridine (1 mL, 10 mmol) was stirred at 60° C. for 7 h. The reaction was then stirred at at 110° C. for 16 h. The reaction was quenched with 0.1N HCl and diluted with DCM. The organic layer was removed and the aqueous phase was extracted with DCM (3×). The combined organics were concentrated. The residue was purified by flash chromatography (0% to 20% (12 min) to 70% (10 min) EtOAc/hexanes) to yield an inseparable mixture of tert-butyl 5-(7-(3-cyclopropylisoxazol-5-yl)-3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)pentanoate and regioisomer tert-butyl 5-(7-(5-cyclopropylisoxazol-3-yl)-3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)pentanoate (17 mg; Yield=63%), MS (M+H)=504.3.

Provenance & Evidence