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

HRID 1642950Notes

Reaction equation

HRID 1642950 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](O)=[O:25])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].O[C:28]1([C:34](=[NH:36])[NH2:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH2:29]1>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH:11]([C:24]3[O:25][N:36]=[C:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:35]=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 667557031-Hydroxybenzene-carboximidamide

Product 1

HCID 58002556[3-(4-Ethylphenyl)-5-(3-phenyl-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 45 mg (0.33 mmol, 1.5 eq.) of 1-hydroxybenzene-carboximidamide were reacted according to the General Method 2. Yield: 76 mg (74% of theory)

Sources & evidence

ORD record
ord-2de1f0c407624b7485e735d8ab3dd4c0
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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