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

HRID 43848Notes

Reaction equation

HRID 43848 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[N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.O1CCOCC1.Br[C:38]1[S:39][C:40]2[C:46]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=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:38]3[S:39][C:40]4[C:46]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:45][CH:44]=[CH:43][C:41]=4[N:42]=3)[CH2:14][C@H:13]2[N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)=[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 86648781tert-butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-pyrrolidin-1-ylpiperidine-1-carboxylate

Product 1

HCID 86648780Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-pyrrolidin-1-ylpiperidin-1-yl)-1,3-benzothiazole-7-carboxylateYield 54%

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-pyrrolidin-1-ylpiperidine-1-carboxylate obtained in Example (201d) (21.0 mg, 0.049 mmol), 4 N hydrochloric acid/1,4-dioxane (2 mL), ethyl 2-bromo-1,3-benzothiazole-7-carboxylate obtained in Example (1f) (16 mg, 0.054 mmol) and sodium carbonate (52 mg, 0.493 mmol), to obtain 14 mg of the title compound (54%) as a pale yellow oily substance.

Sources & evidence

ORD record
ord-9c07968ab3554755a75d7cf0623e9918
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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