Citric Acid → HCID 178522441, compound

HRID 1012088Notes

Reaction equation

HRID 1012088 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([O:21]C)=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].C([O-])(O)=O.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 178488063HCID 178488063, compound

Product 1

HCID 178522441HCID 178522441, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-difluoro-N-[3-(5-methoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (Example 27) (850 mg) and aluminium (III) chloride (220 mg) in toluene (4 ml) was heated at 80° C. for 3 hours, cooled to ambient temperature and saturated aqueous NaHCO3 (4 ml) followed by 5% aqueous citric acid (4 ml) added. The mixture was extracted with EtOAc and organic extract washed with brine, dried (MgSO4) and reduced in vacuo. Residue submitted for preparative LC/MS to give 2,6-difluoro-N-[3-(5-hydroxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (22 mg) as a beige solid. (LC/MS: Rt 2.01, [M+H]+ 356.09).

Workup

  1. temperaturecooled to ambient temperature
  2. additionadded
  3. extractionThe mixture was extracted with EtOAc
  4. extractionorganic extract
  5. washwashed with brine
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-57480b99441c4604bde3324a23dfe1f6
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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