4-Fluoro-n-hydroxybenzimidamide → 1-(Cyclopentylcarbonyl)-3-(4-ethylphenyl)-5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidine

HRID 1642874Notes

Reaction equation

HRID 1642874 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.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[N:34]O)[NH2:33])=[CH:28][CH:27]=1>>[CH:1]1([C:6]([N:8]2[CH2:9][CH:10]([C:22]3[O:23][N:34]=[C:32]([C:29]4[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=4)[N:33]=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 5930004-Fluoro-n-hydroxybenzimidamideHCID 461646851-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-carboxylic acid

Product 1

HCID 580027441-(Cyclopentylcarbonyl)-3-(4-ethylphenyl)-5-[3-(4-fluorophenyl)-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 34 mg (0.22 mmol, 1.1 eq.) of 4-fluoro-N′-hydroxybenzenecarboximidamide were reacted according to the General Method 1. Yield: 45 mg (50% of theory)

Sources & evidence

ORD record
ord-f22ee40721f34a008819d8bbf4b66a4a
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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