Sodium Carbonate → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(propylamino)piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 43856Notes

Reaction equation

HRID 43856 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[NH:18][CH2:19][CH2:20][CH3:21])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Br[C:23]1[S:24][C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:23]3[S:24][C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=3)[CH2:14][C@H:13]2[NH:18][CH2:19][CH2:20][CH3:21])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 86648791cis(+/-)-4-chloro-5-ethyl-N-[3-(propylamino)piperidin-4-yl]-1H-imidazole-2-carboxamide

Product 1

HCID 86648792Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(propylamino)piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 65.2%

Procedure

The same operation as in Example (196c) was performed using cis(±)-4-chloro-5-ethyl-N-[3-(propylamino)piperidin-4-yl]-1H-imidazole-2-carboxamide obtained in Example (205a) (17.0 mg, 0.054 mmol), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (15 mg, 0.060 mmol) and sodium carbonate (17 mg, 0.163 mmol), to obtain 17 mg of the title compound (65%) as a colorless solid.

Sources & evidence

ORD record
ord-f7c692078ebe45498dd7412bbca2cdd4
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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