3-Chlorobenzamidoxime → {3-[3-(3-Chlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

HRID 1643036Notes

Reaction equation

HRID 1643036 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]([OH:28])=O)[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.[Cl:29][C:30]1[CH:31]=[C:32]([C:36](=[N:38]O)[NH2:37])[CH:33]=[CH:34][CH:35]=1>>[Cl:29][C:30]1[CH:31]=[C:32]([C:36]2[N:38]=[C:26]([CH:12]3[CH2:13][CH:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)[CH2:15][N:10]([C:8]([N:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[O:9])[CH2:11]3)[O:28][N:37]=2)[CH:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 27948173-ChlorobenzamidoximeHCID 580023401-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002407{3-[3-(3-Chlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

Procedure

100 mg (0.25 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 99A) and 46.9 mg (0.28 mmol) of 3-chloro-N′-hydroxybenzenecarboximidamide were reacted according to the General Method 1. Yield: 69.5 mg (52% of theory).

Sources & evidence

ORD record
ord-88d38e4e865b4f34afc15ca381970f01
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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