N-hydroxy-2-(4-morpholinyl)ethanimidamide → 4-[(5-[1-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl]-1,2,4-oxadiazol-3-yl)methyl]morpholine

HRID 1642909Notes

Reaction equation

HRID 1642909 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.O[N:30]=[C:31]([NH2:39])[CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[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:23])([F:25])[F:24])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:26]3[O:27][N:39]=[C:31]([CH2:32][N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[N:30]=3)[CH2:10]2)=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 53433451N-hydroxy-2-(4-morpholinyl)ethanimidamideHCID 580025001-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 580022104-[(5-[1-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl]-1,2,4-oxadiazol-3-yl)methyl]morpholine

Procedure

80 mg (0.20 mmol) of 1-(morpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid (Example 44A) and 35 mg (0.22 mmol, 1.1 eq.) of N′-hydroxy-2-morpholin-4-ylethanimidamide were reacted according to the General Method 1. Yield: 28 mg (26% of theory)

Sources & evidence

ORD record
ord-969789c2a88f4b12be8452181bb3c6d0
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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