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

HRID 1425311Notes

Reaction equation

HRID 1425311 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18](OC(C)(C)C)=O)[CH2:14][C@H:13]2[N:25]([CH3:27])[CH3:26])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.O1CCOCC1.BrC1[S:37][C:38]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:39]([CH3:41])[N:40]=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:18]3[S:37][C:38]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:39]([CH3:41])[N:40]=3)[CH2:14][C@H:13]2[N:25]([CH3:26])[CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 204431481,4-Dioxane hydrochlorideHCID 86648777tert-Butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(dimethylamino)-piperidine-1-carboxylate

Product 1

HCID 86648778Ethyl cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(dimethylamino)piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 90.2%

Procedure

The same operation as in Example (196c) was performed using tert-butyl cis(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(dimethylamino)-piperidine-1-carboxylate obtained in Example (200d) (104 mg, 0.260 mmol), 4 N hydrochloric acid/1,4-dioxane (2 mL), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (71.6 mg, 0.286 mmol) and sodium carbonate (551 mg, 5.20 mmol), to obtain 110 mg of the title compound (90%) as a pale yellow solid.

Sources & evidence

ORD record
ord-32a44a2ea4344a90a933acfb239344a1
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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