1-[Ethyl(methyl)carbamoyl]-5-(4-ethylphenyl)piperidine-3-carboxylic acid → 3-[3-(2-Chloropyridin-4-yl)-1,2,4-oxadiazol-5-yl]-N-ethyl-5-(4-ethylphenyl)-N-methylpiperidine-1-carboxamide

HRID 1642917Notes

Reaction equation

HRID 1642917 reaction equation
[CH2:1]([N:3]([CH3:23])[C:4]([N:6]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=2)[CH2:9][CH:8]([C:20](O)=[O:21])[CH2:7]1)=[O:5])[CH3:2].[Cl:24][C:25]1[CH:30]=[C:29]([C:31](=[N:33]O)[NH2:32])[CH:28]=[CH:27][N:26]=1>>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]2[N:33]=[C:20]([CH:8]3[CH2:9][CH:10]([C:12]4[CH:13]=[CH:14][C:15]([CH2:18][CH3:19])=[CH:16][CH:17]=4)[CH2:11][N:6]([C:4]([N:3]([CH2:1][CH3:2])[CH3:23])=[O:5])[CH2:7]3)[O:21][N:32]=2)[CH:28]=[CH:27][N:26]=1

Participants

3

Reactant 2

HCID 580023211-[Ethyl(methyl)carbamoyl]-5-(4-ethylphenyl)piperidine-3-carboxylic acidHCID 1359155502-chloro-N'-hydroxy-4-pyridinecarboximidamide

Product 1

HCID 580027013-[3-(2-Chloropyridin-4-yl)-1,2,4-oxadiazol-5-yl]-N-ethyl-5-(4-ethylphenyl)-N-methylpiperidine-1-carboxamide

Procedure

64 mg (0.20 mmol) of 1-[ethyl(methyl)carbamoyl]-5-(4-ethylphenyl)piperidine-3-carboxylic acid (Example 45A) and 38 mg (0.22 mmol, 1.1 eq.) of 2-chloro-N′-hydroxypyridine-4-carboximidamide were reacted according to the General Method 1. Yield: 13 mg (14% of theory)

Sources & evidence

ORD record
ord-37cfbaaec4b34f1e866c3152a5b7deac
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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