Sodium Carbonate → HCID 86648803, compound

HRID 43865Notes

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[NH:25][CH:26]([CH3:28])[CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.O1CCOCC1.BrC1[S:38][C:39]2[C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:44][CH:43]=[CH:42][C:40]=2[N:41]=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:38][C:39]4[C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:44][CH:43]=[CH:42][C:40]=4[N:41]=3)[CH2:14][C@H:13]2[NH:25][CH:26]([CH3:27])[CH3:28])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

Reactant 4

HCID 10340Sodium Carbonate

HCID 204431481,4-Dioxane hydrochloride

HCID 67073467Ethyl 2-bromobenzo[d]thiazole-7-carboxylate

HCID 86648800HCID 86648800, compound

Product 1

HCID 86648803HCID 86648803, compoundYield 28.1%

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-(isopropylamino)piperidine-1-carboxylate obtained in Example (211a) (20.0 mg, 0.048 mmol), 4 N hydrochloric acid/1,4-dioxane (2 mL), ethyl 2-bromo-1,3-benzothiazole-7-carboxylate obtained in Example (1f) (15 mg, 0.053 mmol) and sodium carbonate (51 mg, 0.483 mmol), to obtain 7 mg of the title compound (28%) as a colorless solid.

Sources & evidence

ORD record: ord-ccc0572c26ea4e6284e29876d12e7e3c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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