3-Methylbutanehydrazide → {3-[5-(2-Methylpropyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

HRID 1643127Notes

Reaction equation

HRID 1643127 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:26]([OH:28])=O)[CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:29][CH:30]([CH3:36])[CH2:31][C:32]([NH:34][NH2:35])=O>>[CH3:29][CH:30]([CH3:36])[CH2:31][C:32]1[O:28][C:26]([CH:11]2[CH2:12][CH:13]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=3)[CH2:14][N:9]([C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[O:8])[CH2:10]2)=[N:35][N:34]=1

Participants

3

Reactant 2

HCID 322833-MethylbutanehydrazideHCID 580025001-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002336{3-[5-(2-Methylpropyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanoneYield 36.6%

Procedure

100 mg (0.249 mmol) of the compound from Example 44A and 32 mg (0.273 mmol) of 3-methylbutanehydrazide were reacted according to the General Method 4. Diastereomer separation of the cis/trans isomer mixture according to Method 14C gave 44 mg of the title compound (cis isomer) and 12 mg of the trans isomer.

Workup

  1. customDiastereomer separation of the cis/trans isomer mixture

Sources & evidence

ORD record
ord-473325ed2b5242cc97fff157aa5cae52
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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