Réaction #155559

Équation de réaction

1,8-Diazabicyclo[5.4.0]undec-7-ene

N-((4aS,5S,7aS)-7a-(2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

→

title compound

Rendement 104.2%

(4aS,5S,7aS)-7a-(2,4-Difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine

Rendement 104.2%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   Températureto cool to RT
2. 2
   Autrethe volatiles were removed in vacuo
3. 3
   AutreThe residue was purified by column chromatography (normal phase, 25 g, Biotage SNAP cartridge KP-Sil, 25 mL per min, gradient 20% to 100% EtOAc in n-hexane)

Mode opératoire

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.99 mL, 6.6 mmol) was added to a stirred suspension of N-((4aS,5S,7aS)-7a-(2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (1.34 g, 3.30 mmol) in dry MeOH (10 mL) at RT under nitrogen. The reaction was stirred and heated at 65° C. overnight, under nitrogen. The reaction was allowed to cool to RT and the volatiles were removed in vacuo. The residue was purified by column chromatography (normal phase, 25 g, Biotage SNAP cartridge KP-Sil, 25 mL per min, gradient 20% to 100% EtOAc in n-hexane) to give the title compound (1.04 g). 1H NMR (400 MHz, CDCl3) δ ppm: 2.78 (dd, J=13.33, 4.03 Hz, 1 H) 2.93-3.01 (m, 1 H) 3.09 (dd, J=13.39, 3.61 Hz, 1 H) 3.83 (dd, J=8.44, 2.45 Hz, 1 H) 4.44-4.56 (m, 3 H) 4.62 (d, J=4.40 Hz, 1 H) 6.75-6.92 (m, 2 H) 7.36-7.47 (m, 1 H).

Source