Lithium hydroxide, monohydrate → HCID 178522445, compound

HRID 1012079Notes

Reaction equation

HRID 1012079 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[C:18]([NH:19][C:20](=[O:29])[C:21]4[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=4[F:28])=[CH:17][NH:16][N:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[F:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([F:27])[C:21]=1[C:20]([NH:19][C:18]1[C:14]([C:11]2[NH:10][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[N:12]=2)=[N:15][NH:16][CH:17]=1)=[O:29]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 1784975902-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazole-4-carboxylic acid methyl ester

Product 1

HCID 178522445HCID 178522445, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazole-4-carboxylic acid methyl ester (220 mg, 0.55 mmol) in THF/water (1:1, 10 ml) was treated with lithium hydroxide hydrate (70 mg, 1.66 mmol) and the mixture stirred at ambient temperature for 18 h. The volatiles were removed in vacuo, the mixture acidified to pH5 by the addition of 2M aqueous hydrochloric acid and the solid formed collected by filtration, washed with water then dried under vacuum to give 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazole-4-carboxylic acid (165 mg) as a brown solid. (LC/MS: Rt 3.28, [M+H]+ 384).

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe mixture acidified to pH5 by the addition of 2M aqueous hydrochloric acid
  3. customthe solid formed
  4. filtrationcollected by filtration
  5. washwashed with water
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-58a3c70c83244b5ba326e907dffdbf3d
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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