1-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid → 4-({3-[3-(2-Chloropyridin-4-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)morpholine

HRID 1642916Notes

Reaction equation

HRID 1642916 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:26](O)=[O:27])[CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:29][C:30]1[CH:35]=[C:34]([C:36](=[N:38]O)[NH2:37])[CH:33]=[CH:32][N:31]=1>>[Cl:29][C:30]1[CH:35]=[C:34]([C:36]2[N:38]=[C:26]([CH:11]3[CH2:12][CH:13]([C:15]4[CH:16]=[CH:17][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=4)[CH2:14][N:9]([C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[O:8])[CH2:10]3)[O:27][N:37]=2)[CH:33]=[CH:32][N:31]=1

Participants

3

Reactant 2

HCID 580025001-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acidHCID 1359155502-chloro-N'-hydroxy-4-pyridinecarboximidamide

Product 1

HCID 580022044-({3-[3-(2-Chloropyridin-4-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)morpholine

Procedure

600 mg (1.49 mmol) of 1-(morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid (Example 44A) and 281 mg (1.64 mmol, 1.1 eq.) of 2-chloro-N′-hydroxypyridine-4-carboximidamide were reacted according to the General Method 1. Yield: 315 mg (39% of theory)

Sources & evidence

ORD record
ord-c9bae9a02a704b75a3e3d1eb41dd1459
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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