Water → HCID 66789376, compound

Participants

Reaction Steps

To solution of 7-amino-4-(4-fluorophenyl)-5-(hydroxymethyl)-2,2-dimethyl-2H -1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 175(3), 117 mg) and pyridine (0.12 mL) in dichloromethane (5 nm) was added dropwise methanesulfonyl chloride (0.085 mL) under ice-cooling, and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was dissolved in methanol (4 mL) and the solution was refluxed for 15 hours. The reaction mixture was concentrated in vacuo, and the resultant residue was purified by column chromatography on silica gel (Solvent; chloroform→chloroform/methanol=85/15) to give N-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H -1,4-benzoxazin-7-yl]methanesulfonamide as a pale yellow powder (40 mg, MS (APCI) m/z; 409 [M+H]+) and N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide as a pale brown powder (52 mg, MS (APCI) m/z; 409 [M+H]+), respectively.

Provenance & Evidence