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

HRID 1425206Notes

Reaction equation

HRID 1425206 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].[S:22]1[CH:26]=[C:25]([C:27](O)=[O:28])[N:24]=[CH:23]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:27]([C:25]3[N:24]=[CH:23][S:22][CH:26]=3)=[O:28])[CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 3042714-Thiazolecarboxylic acidHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648680cis(+/-)-4-Chloro-N-[3-ethoxy-1-(1,3-thiazol-4-ylcarbonyl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamideYield 42.2%

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) and 4-thiazolecarboxylic acid (39 mg, 0.30 mmol) were suspended in DMF (3 mL). The suspension was subjected to the same operation as in Example (138a) to obtain 51.6 mg of the title compound as a colorless solid (42%).

Sources & evidence

ORD record
ord-4352a8bf2d674c41b82cf05770baf1e2
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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