n-Hydroxypivalimidamide → 3-(3-tert-Butyl-1,2,4-oxadiazol-5-yl)-N-ethyl-5-(4-ethylphenyl)-N-methylpiperidine-1-carboxamide

HRID 1642918Notes

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]([OH:22])=O)[CH2:7]1)=[O:5])[CH3:2].O[N:25]=[C:26]([NH2:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>>[C:27]([C:26]1[N:31]=[C:20]([CH:8]2[CH2:9][CH:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=3)[CH2:11][N:6]([C:4]([N:3]([CH2:1][CH3:2])[CH3:23])=[O:5])[CH2:7]2)[O:22][N:25]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

Reactant 2

HCID 2794841n-Hydroxypivalimidamide

HCID 580023211-[Ethyl(methyl)carbamoyl]-5-(4-ethylphenyl)piperidine-3-carboxylic acid

Product 1

HCID 580023533-(3-tert-Butyl-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 26 mg (0.22 mmol, 1.1 eq.) of N′-hydroxy-2,2-dimethylpropanimidamide were reacted according to the General Method 1. Yield: 52 mg (65% of theory)

Sources & evidence

ORD record: ord-02e0d11bf9384a8c9357d4b6caa56f0b
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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