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

Reaction equation

HRID 43724 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].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]

Participants

5

Reactant 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

Product 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-carboxamideYield 16%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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%).

Sources & evidence

ORD record
ord-fda1f2f84818422db1424d820a39fe89
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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