Ammonia → HCID 20114810, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve ammonium acetate (1.3 g, 16.19 mmol) in EtOH (15.69 mL); add 2-(3-oxo-1,4-benzoxazin-4-yl)acetaldehyde (150 mg, 0.78 mmol), sodium cyanoborohydride (155.7 mg, 2.35 mmol), and aqueous ammonia (32%; 5.64 g, 105.91 mmol). Charge a sealable tube with the mixture and seal the tube. Heat to 80° C. and stir overnight. Thereafter allow the mixture to cool to ambient temperature and remove the solvent under reduced pressure. Add EtOAc; wash with brine; NaHCO3 (saturated, aqueous); dry; filter; and concentrate the filtrate under reduced pressure. Purify via flash column chromatography eluting with a step gradient of 5%, 10% and 20% MeOH in DCM. Combine the desired fractions and remove the solvent under reduced pressure to provide the title compound (170 mg, 80%). MS (m/z): 193 (M+1).

Provenance & Evidence