2,6-difluoro-N'-hydroxybenzenecarboximidamide → 3-[3-(2,6-Difluorophenyl)-1,2,4-oxadiazol-5-yl]-N-ethyl-5-(4-ethylphenyl)-N-methylpiperidine-1-carboxamide

HRID 1642915Notes

Reaction equation

HRID 1642915 reaction equation
[CH2:1]([N:3]([CH3:23])[C:4]([N:6]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=2)[CH2:9][CH:8]([C:20]([OH:22])=O)[CH2:7]1)=[O:5])[CH3:2].[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=1[C:32](=[N:34]O)[NH2:33]>>[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=1[C:32]1[N:34]=[C:20]([CH:8]2[CH2:9][CH:10]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH3:19])=[CH:16][CH:17]=3)[CH2:11][N:6]([C:4]([N:3]([CH2:1][CH3:2])[CH3:23])=[O:5])[CH2:7]2)[O:22][N:33]=1

Participants

3

Reactant 2

HCID 34929782,6-difluoro-N'-hydroxybenzenecarboximidamideHCID 580023211-[Ethyl(methyl)carbamoyl]-5-(4-ethylphenyl)piperidine-3-carboxylic acid

Product 1

HCID 580023343-[3-(2,6-Difluorophenyl)-1,2,4-oxadiazol-5-yl]-N-ethyl-5-(4-ethylphenyl)-N-methylpiperidine-1-carboxamide

Procedure

64 mg (0.20 mmol) of 1-[ethyl(methyl)carbamoyl]-5-(4-ethylphenyl)piperidine-3-carboxylic acid (Example 45A) and 38 mg (0.22 mmol, 1.1 eq.) of 2,6-difluoro-N′-hydroxybenzenecarboximidamide were reacted according to the General Method 1. Yield: 23 mg (26% of theory)

Sources & evidence

ORD record
ord-b345f1b92834410aab438a52cc020d3d
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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