N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamide → N-({1-[4-(1,5-Dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

HRID 2388335Notes

Reaction equation

HRID 2388335 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:15])[C:3]1=[O:16].[NH:17]1[CH2:20][CH:19]([NH:21][C:22]([CH2:24][NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:23])[CH2:18]1>>[CH3:1][N:2]1[C:3](=[O:16])[C:4]([CH3:15])=[CH:5][C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([N:17]3[CH2:20][CH:19]([NH:21][C:22]([CH2:24][NH:25][C:26](=[O:37])[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=4)=[O:23])[CH2:18]3)[CH2:10][CH2:9]2)=[CH:7]1

Participants

3

Reactant 2

HCID 59361594N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamideHCID 595418151,3-Dimethyl-5-(4-oxo-cyclohexyl)-1H-pyridin-2-one

Product 1

HCID 46946262N-({1-[4-(1,5-Dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

Procedure

The title compounds were prepared as white solids from the reductive amination of 1,3-dimethyl-5-(4-oxo-cyclohexyl)-1H-pyridin-2-one (as prepared in the previous step) and N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamide using the procedure described in Step F of Example 1.

Sources & evidence

ORD record
ord-0b75d4ce011747b8bf8bf8a0c0526ee5
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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