N'-Hydroxycyclopropanecarboximidamide → {3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(3-hydroxyazetidin-1-yl)methanone

HRID 1643068Notes

Reaction equation

HRID 1643068 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](O)=[O:25])[CH2:9]2)=[O:7])[CH2:3]1.O[N:28]=[C:29]([CH:31]1[CH2:33][CH2:32]1)[NH2:30]>>[CH:31]1([C:29]2[N:30]=[C:24]([CH:10]3[CH2:11][CH:12]([C:14]4[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][CH:15]=4)[CH2:13][N:8]([C:6]([N:4]4[CH2:5][CH:2]([OH:1])[CH2:3]4)=[O:7])[CH2:9]3)[O:25][N:28]=2)[CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 580025781-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 49820082{3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(3-hydroxyazetidin-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 29.6 mg (0.295 mmol) of N′-hydroxycyclopropanecarboximidamide (Example 78A) were reacted according to the General Method 1. Yield: 54 mg (44% of theory).

Sources & evidence

ORD record
ord-65c0c920935641eeacfe914b556c2da3
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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