Sodium Carbonate → cis(+/-)-N-[1-(1,3-Benzothiazol-2-yl)-3-ethoxypiperidin-4-yl]-4-chloro-5-ethyl-1H-imidazole-2-carboxamide

HRID 43721Notes

Reaction equation

HRID 43721 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].Br[C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[N:16]1[CH2:17][CH2:18][C@H:13]([NH:12][C:10]([C:5]2[NH:6][C:7]([CH2:8][CH3:9])=[C:3]([Cl:2])[N:4]=2)=[O:11])[C@H:14]([O:19][CH2:20][CH3:21])[CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6120402-Bromo-1,3-benzothiazoleHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648670cis(+/-)-N-[1-(1,3-Benzothiazol-2-yl)-3-ethoxypiperidin-4-yl]-4-chloro-5-ethyl-1H-imidazole-2-carboxamideYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol), 2-bromobenzothiazole (95 mg, 0.44 mmol) and sodium carbonate (157 mg, 1.48 mmol) were suspended in DMF (3 mL). The suspension was subjected to the same operation as in Example (131b) to obtain 83.4 mg of the title compound as a colorless oily substance (65%).

Sources & evidence

ORD record
ord-41f7bb2b5aa6421ea5ccb6a8839f0226
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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