Reaktion #2285455

Reaktionsgleichung

2-oxaadamantane 1-carbonylchloride

triethylamine

2-Amino-6-fluorobenzoic acid

3,3-difluoro-azetidine hydrochloride

→

title compound

N-{2-[(3 3-difluoroazetidin-1-yl)carbonyl]-3-fluorophenyl}-2-oxatricyclo[3.3.1.13,7]decane-1-carboxamide

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeEvaporation of solvents and flash chromotography over silica gel (20% ethyl acetate/hexane)

Vorschrift

2-Amino-6-fluorobenzoic acid (0.25 g) and 3,3-difluoro-azetidine hydrochloride (0.25 g) were reacted according to the method of Example 332C. The resultant intermediate (0.15 g) was then reacted with 2-oxaadamantane 1-carbonylchloride (1.25 equiv) (prepared from 2-oxaadamantane 1-carboxylic acid and thionyl chloride as in Example 12) and triethylamine (2 equiv) in acetonitrile (10 mL). Evaporation of solvents and flash chromotography over silica gel (20% ethyl acetate/hexane) provided 80 mg of the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.66-2.03 (m, 10H), 2.17 (br s, 2H), 4.36-4.53 (m, 4H), 7.09 (m, 1H), 7.49 (m, 1H), 7.63 (d, 1H), 9.85 (s, 1H); MS (ESI+) m/z 395 (M+H)+.

Quelle