N-({1-[4-(6-Methoxy-pyridin-3-yl)-cyclohex-3-enyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide → N-({1-[4-(6-Methoxy-pyridin-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

HRID 2388299Notes

Reaction equation

HRID 2388299 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:18][CH:17]([NH:19][C:20]([CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)=[O:21])[CH2:16]3)[CH2:11][CH:10]=2)=[CH:5][CH:4]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:16][CH:17]([NH:19][C:20]([CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=4)=[O:21])[CH2:18]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 59541823N-({1-[4-(6-Methoxy-pyridin-3-yl)-cyclohex-3-enyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

Product 1

HCID 46927117N-({1-[4-(6-Methoxy-pyridin-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-({1-[4-(6-Methoxy-pyridin-3-yl)-cyclohex-3-enyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (as prepared in the previous step, 500 mg, 1.02 mmol) from step B in MeOH (40 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-16cb9854be8b4faea75b1f6ba8a9a7dc
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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