Phenylglyoxylic Acid → cis(+/-)-4-Chloro-N-{3-ethoxy-1-[oxo(phenyl)acetyl]piperidin-4-yl}-5-ethyl-1H-imidazole-2-carboxamide

HRID 1425205

Reaction equation

HRID 1425205 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].[C:22]([C:30](O)=[O:31])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:30](=[O:31])[C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 11915Phenylglyoxylic AcidHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648679cis(+/-)-4-Chloro-N-{3-ethoxy-1-[oxo(phenyl)acetyl]piperidin-4-yl}-5-ethyl-1H-imidazole-2-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol) and benzoylformic acid (45 mg, 0.30 mmol) were suspended in DMF (3 mL). The suspension was subjected to the same operation as in Example (138a) to obtain 86.2 mg of the title compound as a colorless amorphous solid (67%).

Sources & evidence

ORD record
ord-3670f20867ff43b8b89ec5697516e7aa
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Linked notes

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