N'-Hydroxybenzenecarboximidamide → (4-Hydroxypiperidin-1-yl) {3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]-piperidin-1-yl}methanone

HRID 1642944Notes

Reaction equation

HRID 1642944 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:27](O)=[O:28])[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.O[N:31]=[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:33]>>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:26])[F:25])=[CH:20][CH:21]=3)[CH2:13][CH:12]([C:27]3[O:28][N:33]=[C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=3)[CH2:11]2)=[O:9])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 69186N'-HydroxybenzenecarboximidamideHCID 580024151-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002185(4-Hydroxypiperidin-1-yl) {3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]-piperidin-1-yl}methanone

Procedure

100 mg (0.24 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid (Example 63A) and 49 mg (0.36 mmol, 1.5 eq.) of N′-hydroxybenzenecarboximidamide were reacted according to the General Method 2. Yield: 58 mg (47% of theory)

Sources & evidence

ORD record
ord-7727d30b57ac4111a78619e57d854410
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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