Sodium Carbonate → cis(+/-)-4-Chloro-N-[3-ethoxy-1-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamide

HRID 43724

Reaktionsgleichung

Reaktionsgleichung von HRID 43724
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].Cl[C:23]1[CH:28]=[CH:27][N:26]([CH3:29])[C:25](=[O:30])[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:23]3[CH:28]=[CH:27][N:26]([CH3:29])[C:25](=[O:30])[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

5

Edukt 3

HCID 10340Sodium CarbonateHCID 154291874-Chloro-1-methylpyridin-2(1H)-oneHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Produkt 1

HCID 86648674cis(+/-)-4-Chloro-N-[3-ethoxy-1-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamideAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (50 mg, 0.15 mmol), 4-chloro-1-methylpyridin-2(1H)-one obtained in Example (137a) (25 mg, 0.17 mmol) and sodium carbonate (78 mg, 0.74 mmol) were suspended in DMSO (1 mL). The suspension was subjected to the same operation as in Example (131b) to obtain 9.8 mg of the title compound as a pale brown amorphous solid (16%).

Quellen und Nachweise

ORD-Eintrag
ord-fda1f2f84818422db1424d820a39fe89
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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