Sodium Carbonate → cis(+/-)-4-Chloro-N-(3-ethoxy-1-pyrimidin-2-ylpiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide

HRID 43723

Reaction equation

HRID 43723 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[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>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:23]3[N:28]=[CH:27][CH:26]=[CH:25][N: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 744042-ChloropyrimidineHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648673cis(+/-)-4-Chloro-N-(3-ethoxy-1-pyrimidin-2-ylpiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamideYield 22.3%

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), 2-chloropyrimidine (51 mg, 0.45 mmol) and sodium carbonate (157 mg, 1.48 mmol) were suspended in DMF (1 mL). The suspension was subjected to the same operation as in Example (131b) to obtain 25.1 mg of the title compound as a white solid (22%).

Sources & evidence

ORD record
ord-346ba7a62f974cd7a72fec0a2a24d51d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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