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

HRID 43539

Reaction equation

HRID 43539 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:17]([NH:18][C:19]([C:21]2[NH:22][C:23]([CH2:27][CH3:28])=[C:24]([Cl:26])[N:25]=2)=[O:20])[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:43]1[S:44][C:45]([C:49]([O:51][CH2:52][CH3:53])=[O:50])=[C:46]([CH3:48])[N:47]=1>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:17]([NH:18][C:19]([C:21]2[NH:22][C:23]([CH2:27][CH3:28])=[C:24]([Cl:26])[N:25]=2)=[O:20])[CH2:16][CH2:15][N:14]([C:43]2[S:44][C:45]([C:49]([O:51][CH2:52][CH3:53])=[O:50])=[C:46]([CH3:48])[N:47]=2)[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 86648552tert-Butyl trans(+/-)-3-{[(benzyloxy)carbonyl]amino}-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylate

Product 1

HCID 86648553Ethyl trans(+/-)-2-(3-{[(benzyloxy)carbonyl]amino}-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateYield 85%

Procedure

The same operation as in Example (1h) was performed using tert-butyl trans(±)-3-{[(benzyloxy)carbonyl]amino}-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylate obtained in Example (79d) (85 mg, 0.17 mmol), sodium carbonate (160 mg, 1.51 mmol) and ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (55 mg, 0.22 mmol), to obtain 82.3 mg of the title compound as a yellow solid (85%).

Sources & evidence

ORD record
ord-30ad2dda8376446bb5802bfb5a838345
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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