Sodium Bicarbonate → HCID 18753123, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 211 mg of the product of Preparation 27 and 274 mg of diethyl ethoxymethylenemalonate is heated under argon at 140° C. for 2 h, then cooled and chromatographed on silica using 2-4% methanol in dichloromethane to provide 230 mg of the intermediate enamide, which is diethyl 2-{[3,7-bis(4-morpholinylmethyl)-2,3-dihydro-4H-1,4-benzoxazin4-yl]methylene}malonate, as an orange foam. This is mixed thoroughly with 1.5 g of polyphosphoric acid, and the mixture is heated at 90° C. for 18 h, then cooled and added to excess aqueous NaHCO3. The mixture is extracted thrice with dichloromethane, and the organic phases dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 2-5% methanol in dichloromethane affords 117 mg of the title compound.

Provenance & Evidence