N-Hydroxynicotinimidamide → 3-{5-[1-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]-1,2,4-oxadiazol-3-yl}pyridine

HRID 1642886Notes

Reaction equation

HRID 1642886 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]([OH:24])=O)[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:26]=[C:27]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[NH2:28]>>[CH:1]1([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH3:21])=[CH:18][CH:19]=3)[CH2:11][CH:10]([C:22]3[O:24][N:28]=[C:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[N:26]=3)[CH2:9]2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 308113N-HydroxynicotinimidamideHCID 461646851-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-carboxylic acid

Product 1

HCID 580026483-{5-[1-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]-1,2,4-oxadiazol-3-yl}pyridine

Procedure

66 mg (0.20 mmol) of 1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-carboxylic acid (Example 7A) and 30 mg (0.22 mmol, 1.1 eq.) of N′-hydroxypyridine-3-carboximidamide were reacted according to the General Method 1. Yield: 37 mg (43% of theory)

Sources & evidence

ORD record
ord-29bcfa00ec244fb9a05f62e522d95f31
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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