N'-Hydroxy-2-methylpropanimidamide → (3-Hydroxyazetidin-1-yl) {3-[3-(propan-2-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]-piperidin-1-yl}methanone

HRID 1643071Notes

Reaction equation

HRID 1643071 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]([NH2:33])[CH:30]([CH3:32])[CH3:31]>>[OH:1][CH:2]1[CH2:3][N:4]([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=3)[CH2:11][CH:10]([C:24]3[O:26][N:33]=[C:29]([CH:30]([CH3:32])[CH3:31])[N:28]=3)[CH2:9]2)=[O:7])[CH2:5]1

Participants

3

Reactant 2

HCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 580025781-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002636(3-Hydroxyazetidin-1-yl) {3-[3-(propan-2-yl)-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 30.7 mg (0.295 mmol) of N′-hydroxy-2-methylpropanimidamide were reacted according to the General Method 1. Yield: 47 mg (39% of theory).

Sources & evidence

ORD record
ord-1e0eb854aea84c6ba1bb501bf74a712a
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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