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

HRID 43730

Reaktionsgleichung

Reaktionsgleichung von HRID 43730
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%).

Quellen und Nachweise

ORD-Eintrag
ord-2ed9b9743456472f927467f61d5c1949
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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