2-[2-Chloro-5-(4-ethoxycarbonyl-piperidin-1-yl)-phenyl]-5-fluoro benzoimidazole-1-carboxylic acid tert-butyl ester → 1-[4-Chloro-3-(5-fluoro-1H-benzoimidazol-2-yl)-phenyl]-piperidine-4-carboxylic acid hydrochloride

HRID 77075Notes

Reaction equation

HRID 77075 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32]CC)=[O:31])[CH2:26][CH2:25]2)[CH:21]=[CH:20][C:19]=1[Cl:35])=O)(C)(C)C>Cl>[ClH:35].[Cl:35][C:19]1[CH:20]=[CH:21][C:22]([N:24]2[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]2)=[CH:23][C:18]=1[C:9]1[NH:8][C:12]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=2[N:10]=1

Participants

3

Reactant 1

HCID 669774172-[2-Chloro-5-(4-ethoxycarbonyl-piperidin-1-yl)-phenyl]-5-fluoro benzoimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 1784797481-[4-Chloro-3-(5-fluoro-1H-benzoimidazol-2-yl)-phenyl]-piperidine-4-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Method 3,4—Step e A mixture of 2-[2-Chloro-5-(4-ethoxycarbonyl-piperidin-1-yl)-phenyl]-5-fluoro-benzoimidazole-1-carboxylic acid tert-butyl ester (0.42 g, 0.84 mmol) in 6N HCl (4 mL) was stirred at room temperature for few minutes and then heated in microwave at 120° C. for 15 minutes. Solvent was removed under vacuum to obtain the title compound in quantitative yield.

Workup

  1. temperatureheated in microwave at 120° C. for 15 minutes
  2. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-d9243b1fbcc14c1cb53598b42971bf62
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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