HCID 178522432, compound → HCID 178519337, compound

HRID 1012076Notes

Reaction equation

HRID 1012076 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]([CH2:21][OH:22])=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]>C(Cl)Cl.CO.O=[Mn]=O>[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]([CH:21]=[O:22])=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 1

HCID 178522432HCID 178522432, compound

Product 1

HCID 178519337HCID 178519337, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 2,6-difluoro-N-[3-(5-hydroxymethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (800 mg, 2.17 mmol) and MnO2 (5.00 g, 57.5 mmol) in CH2Cl2/MeOH (10:1, 110 ml) was stirred at ambient temperature for 5 days. The mixture was filtered through a plug of Celite washing with MeOH and the filtrate reduced in vacuo to give 2,6-difluoro-N-[3-(5-formyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (380 mg, 48%) as a yellow solid. (LC/MS: Rt 3.41, [M+H]+ 368.04).

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. washwashing with MeOH

Sources & evidence

ORD record
ord-7733a6618e454a4ea338df0d1be3d612
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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