2,5-difluoro-N'-hydroxybenzenecarboximidamide → 1-({3-[3-(2,5-Difluorophenyl)-1,2,4-oxadiazol-5-yl]5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-carbonyl)piperidine-4-carbonitrile

HRID 1643065Notes

Reaction equation

HRID 1643065 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([N:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:14][CH:13]([C:27]([OH:29])=O)[CH2:12]2)=[O:10])[CH2:5][CH2:4]1)#[N:2].[F:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[C:38](=[N:40]O)[NH2:39]>>[F:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[C:38]1[N:40]=[C:27]([CH:13]2[CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:16][N:11]([C:9]([N:6]3[CH2:5][CH2:4][CH:3]([C:1]#[N:2])[CH2:8][CH2:7]3)=[O:10])[CH2:12]2)[O:29][N:39]=1

Participants

3

Reactant 2

HCID 43581602,5-difluoro-N'-hydroxybenzenecarboximidamideHCID 580023321-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 580023781-({3-[3-(2,5-Difluorophenyl)-1,2,4-oxadiazol-5-yl]5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-carbonyl)piperidine-4-carbonitrile

Procedure

100 mg (0.244 mmol) of 1-[(4-cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 100A) and 46.2 mg (0.269 mmol) of 2,5-difluoro-N′-hydroxybenzenecarboximidamide (Example 74A) were reacted according to the General Method 1. Yield: 72.5 mg (54% of theory).

Sources & evidence

ORD record
ord-13fd6fa30897458bae8badb7cd184334
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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