Hydrochloric Acid → 2-(3,5-Dichloro-pyridin-4-yl-amino)-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 578055Notes

Reaction equation

HRID 578055 reaction equation
C[O:2][C:3]([C:5]1[CH:23]=[CH:22][C:8]2[N:9]([CH3:21])[C:10]([NH:12][C:13]3[C:18]([Cl:19])=[CH:17][N:16]=[CH:15][C:14]=3[Cl:20])=[N:11][C:7]=2[CH:6]=1)=[O:4].Cl>CO.[OH-].[Na+]>[Cl:19][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:20])[C:13]=1[NH:12][C:10]1[N:9]([CH3:21])[C:8]2[CH:22]=[CH:23][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672335772-(3,5-Dichloro-pyridin-4-yl-amino)-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester

Product 1

HCID 672326622-(3,5-Dichloro-pyridin-4-yl-amino)-1-methyl-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A mixture of the product obtained at (547a) (240 mg, 0.68 mmol) in 10 mL methanol and 5 mL 4M NaOH (aq) was stirred at ambient temperature for 2 h, the another 5 mL 4M NaOH (aq) were added and the mixture stirred for 16 h at ambient temperature. The mixture was acidified by addition of 4M HCl (aq), the precipitate was filtered, washed with water and dried at 70° C.

Workup

  1. additionA mixture of the product
  2. stirringthe mixture stirred for 16 h at ambient temperature
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried at 70° C.

Sources & evidence

ORD record
ord-d9d05c5725f449d4bf9d9ac3862435d2
Source dataset
uspto-grants-2015_05
Patent number
US09040565B2

Reaction notes

Loading…