1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 70495591, compound

Participants

Reaction Conditions

Reaction Steps

N-((4aS,5S,7aS)-7a-(2,3-Difluorophenyl)-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (2.00 g) was dissolved in methanol (250 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.53 g) was added, and the solution was heated to reflux (heating block temperature 80° C.). After 3 h, the reaction mixture was concentrated under reduced pressure, diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic portions were dried over MgSO4, evaporated, and the residue purified by silica gel column chromatography (0% to 50% EtOAc in hexanes) to afford the title compound (1.42 g). 1H NMR (400 MHz, CDCl3) δ ppm 2.86 (dd, J=13.6, 3.8 Hz, 1 H), 3.15 (dd, J=13.8, 3.2 Hz, 1 H), 3.27-3.42 (m, 1 H), 3.93 (dd, J=8.2, 1.9 Hz, 1 H), 4.39-4.78 (m, 4 H), 6.96-7.25 (m, 3 H)

Provenance & Evidence