1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68173769, compound

Participants

Reaction Conditions

Reaction Steps

N-((4aS,5S,7aS)-5-(difluoromethyl)-7a-(2,3-difluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide, obtained in Preparation Example 1-(8), (891 mg) was dissolved in methanol (10 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.02 g) was added, and the solution was heated to reflux (heating block temperature 70° C.). After 16 h, the reaction mixture was cooled, concentrated under reduced pressure, and the residue purified by silica gel column chromatography (0% to 80% EtOAc in hexanes) to afford the title compound (565 mg). 1H NMR (400 MHz, CDCl3) δ ppm 2.88 (dd, J=13.4, 4.0 Hz, 1H), 3.13 (dd, J=13.6, 3.3 Hz, 1H), 3.24 (dt, J=7.7, 3.7 Hz, 1H), 3.89 (d, J=8.3 Hz, 1H), 4.33-4.70 (m, 4H), 5.94 (td, J=56.3, 3.8 Hz, 1H), 7.05-7.25 (m, 3H)

Provenance & Evidence