Sodium Carbonate → Ethyl trans(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-[(1-ethylpropyl)amino]piperidin-1-yl)-1,3-benzothiazole-7-carboxylate

HRID 43871Notes

Reaction equation

HRID 43871 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(OC(C)(C)C)=O)[CH2:14][C@H:13]2[NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.O1CCOCC1.Br[C:39]1[S:40][C:41]2[C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=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:39]3[S:40][C:41]4[C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46][CH:45]=[CH:44][C:42]=4[N:43]=3)[CH2:14][C@H:13]2[NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 67073467Ethyl 2-bromobenzo[d]thiazole-7-carboxylateHCID 86648808HCID 86648808, compound

Product 1

HCID 86648811Ethyl trans(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-[(1-ethylpropyl)amino]piperidin-1-yl)-1,3-benzothiazole-7-carboxylateYield 56%

Procedure

The same operation as in Example (196c) was performed using tert-butyl trans(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-[(1-ethylpropyl)amino]piperidine-1-carboxylate obtained in Example (215a) (16.0 mg, 0.036 mmol), 4 N hydrochloric acid/1,4-dioxane (1 mL), ethyl 2-bromo-1,3-benzothiazole-7-carboxylate obtained in Example (1f) (11 mg, 0.040 mmol) and sodium carbonate (38 mg, 0.362 mmol), to obtain 11 mg of the title compound (56%) as a pale yellow oily substance.

Sources & evidence

ORD record
ord-b11f1bd5f9b54539a970d6e5d62eefea
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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