N'-Hydroxybenzenecarboximidamide → 1-(Cyclopentylcarbonyl)-3-(4-ethylphenyl)-5-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidine

HRID 1642859Notes

Reaction equation

HRID 1642859 reaction equation
[CH:1]1([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=3)[CH2:11][CH:10]([C:22](O)=[O:23])[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:26]=[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH2:28]>>[CH:1]1([C:6]([N:8]2[CH2:9][CH:10]([C:22]3[O:23][N:28]=[C:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:26]=3)[CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=3)[CH2:13]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 69186N'-HydroxybenzenecarboximidamideHCID 461646851-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-carboxylic acid

Product 1

HCID 580023451-(Cyclopentylcarbonyl)-3-(4-ethylphenyl)-5-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidine

Procedure

329 mg (1.0 mmol) of 1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-carboxylic acid (Example 7A) and 149 mg (1.1 mmol, 1.1 eq.) of N′-hydroxybenzenecarboximidamide were reacted according to the General Method 1. Yield: 235 mg (55% of theory)

Sources & evidence

ORD record
ord-04416fb426a046228b297bb6b35fb6c4
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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