Hydrochloric Acid → 1-(cyclopropylmethyl)-2-[(5-ethoxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carboxylic acid

HRID 1796484Notes

Reaction equation

HRID 1796484 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11]C(C#N)=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][N:18]=2)[CH2:3][CH2:2]1.[CH3:26][CH2:27][OH:28].[OH-:29].[K+].Cl>O>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:26]([C:27]([OH:29])=[O:28])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][N:18]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 221812731-(cyclopropylmethyl)-2-[(5-ethoxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carbonitrile

Product 1

HCID 221814061-(cyclopropylmethyl)-2-[(5-ethoxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution 1-(cyclopropylmethyl)-2-[(5-ethoxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carbonitrile (400 mg, 1.203 mmol) in 1:1 EtOH:H2O (12 mL) was added KOH (269 mg, 4.81 mmol). The resulting mixture was refluxed for 36 h. The mixture was acidified with 1 N HCl to pH˜6.0. The precipitate (397 mg, 94%) was used in the subsequent step without further purification. MS (ESI) (M+H)+=352.

Workup

  1. temperatureThe resulting mixture was refluxed for 36 h
  2. customThe precipitate (397 mg, 94%) was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-c9f235c845d743e785a361029dc9dee4
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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