1-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid → (3-Hydroxyazetidin-1-yl) {3-(3-{[1-(hydroxymethyl)cyclopropyl]methyl}-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

HRID 1643000Notes

Reaction equation

HRID 1643000 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]([NH2:36])[CH2:30][C:31]1([CH2:34][OH:35])[CH2:33][CH2:32]1>>[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:25][N:36]=[C:29]([CH2:30][C:31]4([CH2:34][OH:35])[CH2:33][CH2:32]4)[N:28]=3)[CH2:9]2)=[O:7])[CH2:5]1

Participants

3

Reactant 2

HCID 580025781-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acidHCID 79009133N'-Hydroxy-2-[1-(hydroxymethyl)cyclopropyl]ethanimidamide

Product 1

HCID 58002749(3-Hydroxyazetidin-1-yl) {3-(3-{[1-(hydroxymethyl)cyclopropyl]methyl}-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

Procedure

100 mg (0.27 mmol) of the compound from Example 101A and 67 mg (0.40 mmol) of the compound from Example 67A were reacted according to the General Method 2. Yield: 33 mg (26% of theory)

Sources & evidence

ORD record
ord-5a28443b942448a883c3fe2ff79a38c9
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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