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Hydrochloric Acid → 2-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1189654
Notes
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Reaction equation

HRID 1189654 reaction equation
C([O:3][C:4]([C:6]1[C:32]([N:33]2[CH2:38][CH2:37][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:35][CH2:34]2)=[CH:31][C:9]2[N:10]([CH3:30])[C:11]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:15]=3[Cl:29])=[N:12][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[Cl:29][C:15]1[C:16]([CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[NH:13][C:11]1[N:10]([CH3:30])[C:9]2[CH:31]=[C:32]([N:33]3[CH2:34][CH2:35][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:37][CH2:38]3)[C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 679575762-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester

Product 1

HCID 679575572-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents

1
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester (550 mg, 0.86 mmol), 1 N NaOH-solution (10 ml) and dioxane (20 ml) is stirred for 24 h at 100° C. and acidified with 1 N HCl (to pH ˜5). The mixture is extracted with EtOAc and the organic layer is washed with brine, dried with Na2SO4, filtered and concentrated.

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. washthe organic layer is washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b63d96f5f1db4cd9a7abff6f57dca4f3
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08674113B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes