N-Hydroxybutyramidine → 1-(Cyclopentylcarbonyl)-3-(4-ethylphenyl)-5-(3-propyl-1,2,4-oxadiazol-5-yl)piperidine

HRID 1642904Notes

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]([NH2:31])[CH2:28][CH2:29][CH3:30]>>[CH:1]1([C:6]([N:8]2[CH2:9][CH:10]([C:22]3[O:24][N:31]=[C:27]([CH2:28][CH2:29][CH3:30])[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])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 2794811N-Hydroxybutyramidine

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

Product 1

HCID 580022961-(Cyclopentylcarbonyl)-3-(4-ethylphenyl)-5-(3-propyl-1,2,4-oxadiazol-5-yl)piperidine

Procedure

66 mg (0.20 mmol) of 1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-carboxylic acid (Example 7A) and 22 mg (0.22 mmol, 1.1 eq.) of N′-hydroxybutanimidamide were reacted according to the General Method 1. Yield: 12 mg (15% of theory)

Sources & evidence

ORD record: ord-f4e66cb8588d4387bcaaed8563ad46c7
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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