Sodium Hydroxide → 2-{2,6-Dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1189705Notes

Reaction equation

HRID 1189705 reaction equation
C([O:3][C:4]([C:6]1[C:26]([N:27]2[CH2:32][CH2:31][CH:30]([C:33]([F:36])([F:35])[F:34])[CH2:29][CH2:28]2)=[CH:25][C:9]2[N:10]([CH3:24])[C:11]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH2:21][NH2:22])[C:15]=3[Cl:23])=[N:12][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+]>CO>[Cl:23][C:15]1[C:16]([CH2:21][NH2:22])=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[NH:13][C:11]1[N:10]([CH3:24])[C:9]2[CH:25]=[C:26]([N:27]3[CH2:32][CH2:31][CH:30]([C:33]([F:36])([F:35])[F:34])[CH2:29][CH2:28]3)[C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 679575112-{2,6-Dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester

Product 1

HCID 679573152-{2,6-Dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-{2,6-dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester (5.83 g, 10 mmol), 50% aq NaOH-solution (25 ml) and MeOH (100 ml) is stirred for 2.5 h at rt. The mixture is concentrated and slowly added to ice-cooled 12 M aq HCl (39.5 mL). Then aq NaHCO3 solution is added (to pH 8) and the resulting precipitate is collected by filtration and dried.

Workup

  1. concentrationThe mixture is concentrated
  2. additionslowly added to ice-
  3. temperaturecooled 12 M aq HCl (39.5 mL)
  4. additionThen aq NaHCO3 solution is added (to pH 8)
  5. filtrationthe resulting precipitate is collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-1ab53163a30c4e09a115f1f966775f28
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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