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

HRID 1425195Notes

Reaction equation

HRID 1425195 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].Br[C:23]1[S:24][CH:25]=[CH:26][N:27]=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[S:24][CH:25]=[CH:26][N:27]=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 764302-BromothiazoleHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648669cis(+/-)-4-Chloro-N-[3-ethoxy-1-(1,3-thiazol-2-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamideYield 40.2%

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-bromothiazole (0.040 mL, 0.44 mmol) and sodium carbonate (157 mg, 1.48 mmol) were suspended in DMF (3 mL). The suspension was subjected to the same operation as in Example (131b) to obtain 45.8 mg of the title compound as a colorless oily substance (40%).

Sources & evidence

ORD record
ord-4f496c7606b5474eace903e45649ac9b
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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