N'-hydroxy-2-phenylethanimidamide → {3-(3-Benzyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

HRID 1643041Notes

Reaction equation

HRID 1643041 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:26](O)=[O:27])[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.O[N:30]=[C:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([C:31]1[N:39]=[C:26]([CH:12]2[CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:15][N:10]([C:8]([N:5]3[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]3)=[O:9])[CH2:11]2)[O:27][N:30]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 2731007N'-hydroxy-2-phenylethanimidamideHCID 580023401-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002354{3-(3-Benzyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

Procedure

100 mg (0.250 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 99A) and 41.3 mg (0.275 mmol) of N′-hydroxy-2-phenylethanimidamide were reacted according to the General Method 1. Yield: 61.5 mg (47% of theory).

Sources & evidence

ORD record
ord-43a50edbe69b4422aaeaed59b82c4eda
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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