N-{[1-(4-Benzo[1,3]-dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide → N-[2-[[1-[4-(1,3-benzodioxol-5-yl)cyclohexyl]azetidin-3-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:15][CH2:14][CH:13]([N:16]4[CH2:19][CH:18]([NH:20][C:21]([CH2:23][NH:24][C:25](=[O:36])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=5)=[O:22])[CH2:17]4)[CH2:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1>CO.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH2:11][CH2:12][CH:13]([N:16]4[CH2:17][CH:18]([NH:20][C:21]([CH2:23][NH:24][C:25](=[O:36])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=5)=[O:22])[CH2:19]4)[CH2:14][CH2:15]3)=[CH:9][C:4]=2[O:3][CH2:2]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N-{[1-(4-Benzo[1,3]dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide (as prepared in the previous step, 250 mg, 0.5 mmol) in MeOH (20 mL) was driven through an H-Cube® Continuous-flow Hydrogenation reactor (ThalesNano, Budapest, Hungary) under full hydrogen mode at room temperature using a 5% Pd/C cartridge. The resulting solution was concentrated and purified by silica gel column on a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the two title compounds as white solids.