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

HRID 43728Notes

Reaction equation

HRID 43728 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]([C:29]2[S:30][C:31]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:32]([CH3:34])[N:33]=2)[C:25](=[O:40])[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]([C:29]4[S:30][C:31]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:32]([CH3:34])[N:33]=4)[C:25](=[O:40])[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 67548707Ethyl 2-(4-chloro-2-oxopyridin-1(2H)-yl)-4-methyl-1,3-thiazole-5-carboxylateHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648677Ethyl cis(+/-)-2-[4-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-2-oxopyridin-1(2H)-yl]-4-methyl-1,3-thiazole-5-carboxylateYield 6.5%

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) (100 mg, 0.297 mmol), ethyl 2-(4-chloro-2-oxopyridin-1(2H)-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (140a) (106 mg, 0.355 mmol) and sodium carbonate (157 mg, 1.48 mmol) were suspended in DMSO (1 mL). The suspension was subjected to same operation as in Example (131b) to obtain 10.8 mg of the title compound as a pale yellow solid (6%).

Sources & evidence

ORD record
ord-e63b17a478fb425e9d46e4b98a242d68
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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