n-Hydroxypivalimidamide → {3-(3-tert-Butyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}(4-hydroxy-piperidin-1-yl)methanone

HRID 1642949Notes

Reaction equation

HRID 1642949 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]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:27](O)=[O:28])[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.O[N:31]=[C:32]([NH2:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>>[C:33]([C:32]1[N:37]=[C:27]([CH:12]2[CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:15][N:10]([C:8]([N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)=[O:9])[CH2:11]2)[O:28][N:31]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

3

Reactant 2

HCID 2794841n-HydroxypivalimidamideHCID 580024151-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002257{3-(3-tert-Butyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}(4-hydroxy-piperidin-1-yl)methanone

Procedure

100 mg (0.24 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid (Example 63A) and 42 mg (0.36 mmol, 1.5 eq.) of N′-hydroxy-2,2-dimethylpropanimidamide were reacted according to the General Method 2. Yield: 60 mg (51% of theory)

Sources & evidence

ORD record
ord-156375abb31542c9968a488ba8dde77a
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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