{5-[(6-Methyl-4'-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester → 6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-amino-indan-5-yl)-amide
Reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18]([C:20]3[C:21]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:19])[CH:14]=2)[CH2:9]1)(C)(C)C>C(O)=O>[NH2:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18]([C:20]3[C:21]([C:27]4[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=4)=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:19])[CH:14]=2)[CH2:9]1Participants
3
Procedure
A solution of {5-[(6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester (5.19 g, 10.5 mmol) in formic acid (40 mL) is heated to 40° C. with stirring. After 3 h, the reaction mixture is cooled to room temperature and stirring is continued for 16 h. The reaction mixture is concentrated under reduced pressure and the resulting oil dissolved in ethyl acetate. The organic layer is washed with 8% NaHCO3 solution until the aqueous layer remains basic at which point a precipitate forms in the organic layer. The precipitate is collected by filtration to give N-(2-aminoindan-5-yl)-6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxamide.