HCID 178522442, compound → HCID 178519447, compound

HRID 1012066Notes

Reaction equation

HRID 1012066 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][CH:19]=[C:20]([CH2:21][OH:22])[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][CH:19]=[C:20]([CH:21]=[O:22])[C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 1

HCID 178522442HCID 178522442, compound

Product 1

HCID 178519447HCID 178519447, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 2,6-difluoro-N-[3-(4-hydroxymethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (200 mg, 0.54 mmol) and MnO2 (500 mg) in CH2Cl2/MeOH (5:1, 12 ml) was stirred at ambient temperature for 18 h, then filtered through Celite and reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:3, 1:2)] to give 2,6-difluoro-N-[3-(4-formyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (30 mg) as a cream solid.

Workup

  1. filtrationfiltered through Celite
  2. customThe residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:3, 1:2)]

Sources & evidence

ORD record
ord-1a43fd22965846d8a3b644a5458f331b
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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