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

HRID 1642952Notes

Reaction equation

HRID 1642952 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:24](O)=O)[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].[Cl:27][C:28]1[CH:29]=[C:30]([C:34](=[N:36][OH:37])[NH2:35])[CH:31]=[CH:32][CH:33]=1>>[Cl:27][C:28]1[CH:29]=[C:30]([C:34]2[N:35]=[C:24]([CH:11]3[CH2:10][CH:9]([C:6]4[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=4)[CH2:14][N:13]([C:15]([N:17]4[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]4)=[O:16])[CH2:12]3)[O:37][N:36]=2)[CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 27948173-ChlorobenzamidoximeHCID 580026415-(4-Ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid

Product 1

HCID 58002577{3-[3-(3-Chlorophenyl)-1,2,4-oxadiazol-5-yl]-5-(4-ethylphenyl)piperidin-1-yl}(4-hydroxy-piperidin-1-yl)methanone

Procedure

80 mg (0.22 mmol) of 5-(4-ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid (Example 59A) and 57 mg (0.33 mmol, 1.5 eq.) of 3-chloro-N′-hydroxybenzenecarboximidamide were reacted according to the General Method 2. Yield: 86 mg (78% of theory)

Sources & evidence

ORD record
ord-59364f0976a74535a3d39e0f27fa1f0c
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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