Sodium Carbonate → HCID 86648797, compound

HRID 1425328Notes

Reaction equation

HRID 1425328 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][CH2:26][CH3:27])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.O1CCOCC1.BrC1[S:37][C:38]2[C:44]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:43][CH:42]=[CH:41][C:39]=2[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]4[C:44]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:43][CH:42]=[CH:41][C:39]=4[N:40]=3)[CH2:14][C@H:13]2[NH:25][CH2:26][CH3:27])=[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 86648794tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(ethylamino)piperidine-1-carboxylate

Product 1

HCID 86648797HCID 86648797, compoundYield 48%

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-(ethylamino)piperidine-1-carboxylate obtained in Example (207a) (25.0 mg, 0.063 mmol), 4 N hydrochloric acid/1,4-dioxane (1 mL), ethyl 2-bromo-1,3-benzothiazole-7-carboxylate obtained in Example (1f) (21 mg, 0.075 mmol) and sodium carbonate (66 mg, 0.625 mmol), to obtain 15 mg of the title compound (48%) as a colorless solid.

Sources & evidence

ORD record
ord-0c93f6842a884ddd82787aad47229dcd
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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