1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 73507167, compound

Participants

Reaction Conditions

Reaction Steps

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.5 mL, 3 mmol) was added to a suspension of N-[(4aR,6S,8aS)-8a-(2,4-difluorophenyl)-6-methyl-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C22) (1.40 g, 3.48 mmol) in methanol (100 mL), and the resulting mixture was heated at 80° C. for 18 hours. After removal of solvent in vacuo, the residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate; the aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification via silica gel chromatography (Eluent: ethyl acetate) afforded the product as a white solid. Yield: 840 mg, 2.82 mmol, 81%. LCMS m/z 299.2 [M+H+]. 1H NMR (400 MHz, CD3OD) δ 7.30-7.38 (m, 1H), 6.92-7.00 (m, 2H), 4.08 (dd, J=11.1, 2.2 Hz, 1H), 3.69-3.78 (m, 1H), 3.65 (d, J=11.1 Hz, 1H), 2.83-2.93 (m, 2H), 2.62-2.68 (m, 1H), 1.65-1.76 (m, 1H), 1.54 (ddd, J=13.1, 4.1, 2.4 Hz, 1H), 1.22 (d, J=6.2 Hz, 3H).

Provenance & Evidence