n-Hydroxypivalimidamide → {3-(3-tert-Butyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(3-hydroxy-azetidin-1-yl)methanone
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]([NH2:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>>[C:30]([C:29]1[N:34]=[C:24]([CH:10]2[CH2:11][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)[CH2:13][N:8]([C:6]([N:4]3[CH2:3][CH:2]([OH:1])[CH2:5]3)=[O:7])[CH2:9]2)[O:26][N:28]=1)([CH3:33])([CH3:32])[CH3:31]Participants
3
Procedure
100 mg (0.269 mmol) of 1-[(3-hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 101A) and 34.3 mg (0.295 mmol) of N′-hydroxy-2,2-dimethylpropanimidamide were reacted according to the General Method 1. Yield: 45 mg (37% of theory).
Sources & evidence
- ORD record
- ord-c28e545a2baf49f8b6ebdadffd857117
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119663B2
Reaction notes
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