3-fluoro-N'-hydroxybenzene-1-carboximidamide → 1-({3-[3-(3-Fluorophenyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-carbonyl)piperidine-4-carbonitrile

HRID 1642995Notes

Reaction equation

HRID 1642995 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]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:14][CH:13]([C:28]([OH:30])=O)[CH2:12]2)=[O:10])[CH2:5][CH2:4]1)#[N:2].[F:31][C:32]1[CH:33]=[C:34]([C:38](=[N:40]O)[NH2:39])[CH:35]=[CH:36][CH:37]=1>>[F:31][C:32]1[CH:33]=[C:34]([C:38]2[N:40]=[C:28]([CH:13]3[CH2:14][CH:15]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]([F:26])([F:25])[F:27])=[CH:19][CH:18]=4)[CH2:16][N:11]([C:9]([N:6]4[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]4)=[O:10])[CH2:12]3)[O:30][N:39]=2)[CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 40909723-fluoro-N'-hydroxybenzene-1-carboximidamideHCID 580027061-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 580022241-({3-[3-(3-Fluorophenyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-carbonyl)piperidine-4-carbonitrile

Procedure

85 mg (0.20 mmol) of 1-[(4-cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]-piperidine-3-carboxylic acid (Example 108A) and 49 mg (0.3 mmol) of 3-fluoro-N′-hydroxybenzenecarboximidamide were reacted according to the General Method 2. Yield: 69 mg (63% of theory).

Sources & evidence

ORD record
ord-627b7ad2f27a4046b7c461ea2afd2d92
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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