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

HRID 43841

Reaction equation

HRID 43841 reaction equation
[Cl:1][C@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[NH:12][C:13]([CH2:17][CH3:18])=[C:14]([Cl:16])[N:15]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19](OC(C)(C)C)=O)[CH2:3]1.Cl.O1CCOCC1.BrC1[S:35][C:36]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:37]([CH3:39])[N:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:1][C@H:2]1[C@@H:7]([NH:8][C:9]([C:11]2[NH:12][C:13]([CH2:17][CH3:18])=[C:14]([Cl:16])[N:15]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19]2[S:35][C:36]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:37]([CH3:39])[N:38]=2)[CH2:3]1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 204431481,4-Dioxane hydrochlorideHCID 86648771tert-Butyl cis(+/-)-3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylate

Product 1

HCID 86648773Ethyl cis(+/-)-2-(3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 40.4%

Procedure

The same operation as in Example (196c) was performed using tert-butyl cis(±)-3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylate obtained in Example (198b) (101 mg, 0.258 mmol), 4 N hydrochloric acid/1,4-dioxane (2 mL), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (71.0 mg, 0.284 mmol) and sodium carbonate (547 mg, 5.16 mmol), to obtain 48 mg of the title compound (40%) as a pale yellow solid.

Sources & evidence

ORD record
ord-bc05155f090d4530b8b440811e6747f4
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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