N-Hydroxyacetamidine → (3-Hydroxyazetidin-1-yl){3-(3-methyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

HRID 1643069Notes

Reaction equation

HRID 1643069 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH2:11][CH:10]([C:24]([OH:26])=O)[CH2:9]2)=[O:7])[CH2:3]1.O[N:28]=[C:29]([NH2:31])[CH3:30]>>[OH:1][CH:2]1[CH2:3][N:4]([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=3)[CH2:11][CH:10]([C:24]3[O:26][N:31]=[C:29]([CH3:30])[N:28]=3)[CH2:9]2)=[O:7])[CH2:5]1

Participants

3

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 580025781-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002286(3-Hydroxyazetidin-1-yl){3-(3-methyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

Procedure

100 mg (0.269 mmol) of 1-[(3-hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 101A) and 21.9 mg (0.269 mmol) of N′-hydroxyethanimidamide were reacted according to the General Method 1. Yield: 41.6 mg (32% of theory).

Sources & evidence

ORD record
ord-03aa821010cb41d4a7d10c37e7eb565b
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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