HCID 21884201, compound → HCID 21884197, compound

HRID 722420Notes

Reaction equation

HRID 722420 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[CH:19]=[CH:20][C:21]([CH2:23][OH:24])=[CH:22][C:12]=3[N:11]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2]>CC(C)=O.[O-2].[Mn+4].[O-2]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[CH:19]=[CH:20][C:21]([CH:23]=[O:24])=[CH:22][C:12]=3[N:11]=2)=[O:8])=[CH:25][CH:26]=1)#[N:2]

Participants

4

Reactant 1

HCID 21884201HCID 21884201, compound

Product 1

HCID 21884197HCID 21884197, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 4-cyano-N-[5-hydroxymethyl-1-(2-methoxy-ethyl)-1H-benzimidazol-2-yl]-benzamide (15.4 mg, 0.042 mmol) in acetone (2 mL) was added manganese (IV) oxide (43 mg, 0.42 mmol). After stirring overnight, the black suspension was filtered thru diatomaceous earth and the filtrate concentrated. The filtrate was dissolved in acetone and run through a 2 g SepPak silica gel cartridge to afford 4-cyano-N-[5-formyl-1-(2-methoxy-ethyl)-1H-benzimidazol-2-yl]-benzamide as a white solid (13 mg, 84%).

Workup

  1. filtrationthe black suspension was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutionThe filtrate was dissolved in acetone

Sources & evidence

ORD record
ord-2771afa42277450688a0f9580f476f48
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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