5-(4-Ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid → {3-(4-Ethylphenyl)-5-[3-(pyrimidin-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

HRID 1642974Notes

Reaction equation

HRID 1642974 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:24]([OH:26])=O)[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].O[N:28]=[C:29]([C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[NH2:30]>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH:11]([C:24]3[O:26][N:30]=[C:29]([C:31]4[N:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[N:28]=3)[CH2:12][N:13]([C:15]([N:17]3[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]3)=[O:16])[CH2:14]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 580026415-(4-Ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acidHCID 136195713N'-hydroxypyrimidine-2-carboximidamide

Product 1

HCID 58002363{3-(4-Ethylphenyl)-5-[3-(pyrimidin-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

Procedure

80 mg (0.22 mmol) of 5-(4-ethylphenyl)-1-[(4-hydroxypiperidin-1-yl)carbonyl]piperidine-3-carboxylic acid (Example 59A) and 46 mg (0.33 mmol) of N′-hydroxypyrimidine-2-carboximidamide were reacted according to the General Method 2. Yield: 66 mg (64% of theory)

Sources & evidence

ORD record
ord-900564ad4de641ff9d379d7e43d2a31c
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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