Sodium Bicarbonate → HCID 178468196, compound

HRID 43747Notes

Reaction equation

HRID 43747 reaction equation
C(=O)(O)[O-].[Na+].Cl.[Cl:7][C:8]1[N:9]=[C:10]([C:15]([NH:17][C@H:18]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]2[O:24][CH2:25][CH3:26])=[O:16])[NH:11][C:12]=1[CH2:13][CH3:14]>C(OCC)(=O)C>[Cl:7][C:8]1[NH:9][C:10]([C:15]([NH:17][C@H:18]2[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]2[O:24][CH2:25][CH3:26])=[O:16])=[N:11][C:12]=1[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 178468196HCID 178468196, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate and saturated sodium bicarbonate solution were added to cis(±)-4-chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (0.100 g, 0.296 mmol), and the aqueous layer was extracted with ethyl acetate. Thereafter, drying over anhydrous sodium sulfate gave cis(±)-4-{[(5-chloro-4-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidine. This and 3-{(S)-2-methoxycarbonylpyrrolidine-1-carbonyl}-3-methyl-1H-imidazol-3-ium iodide obtained in Example (151b) (0.162 g, 0.444 mmol) were dissolved in dichloromethane (5 ml), and the solution was stirred at room temperature for 24 hours. Water and ethyl acetate were added to the reaction solution, followed by extraction with ethyl acetate and further extraction with dichloromethane. The organic layers were combined and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=1/1, then methanol/ethyl acetate=0/100, 5/95, 10/90) to obtain 38 mg of the crude title compound. This was further purified by thin layer silica gel chromatography (developing solvent: methanol/dichloromethane=5/95) to obtain 24 mg of the title compound as a colorless oily substance (18%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. dry with materialThereafter, drying over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-159a614a1f2c4bc798b4f9b46be2d62a
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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