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

HRID 1893221Notes

Reaction equation

HRID 1893221 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]1

Participants

4

Reactant 1

HCID 56680600N-{[1-(4-Benzo[1,3]-dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide

Product 1

HCID 49763568N-[2-[[1-[4-(1,3-benzodioxol-5-yl)cyclohexyl]azetidin-3-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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.

Workup

  1. customat room temperature
  2. concentrationThe resulting solution was concentrated
  3. custompurified by silica gel column on a CombiFlash® system
  4. customto afford the two title compounds as white solids

Sources & evidence

ORD record
ord-499540895df74c1ba47809622cc1264e
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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