N-Hydroxynicotinimidamide → (4-Hydroxypiperidin-1-yl) {3-[3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

HRID 1643040Notes

Reaction equation

HRID 1643040 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]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:26](O)=[O:27])[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.O[N:30]=[C:31]([C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[NH2:32]>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:20][CH:21]=3)[CH2:13][CH:12]([C:26]3[O:27][N:32]=[C:31]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[N:30]=3)[CH2:11]2)=[O:9])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 308113N-HydroxynicotinimidamideHCID 580023401-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002733(4-Hydroxypiperidin-1-yl) {3-[3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

Procedure

100 mg (0.250 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid (Example 99A) and 37.7 mg (0.275 mmol) of N′-hydroxypyridine-3-carboximidamide were reacted according to the General Method 1. Yield: 26.0 mg (21% of theory).

Sources & evidence

ORD record
ord-7ead52a831b14a868c3f0fe64095c905
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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