Potassium Cyanide → HCID 22349407, compound

HRID 896309Notes

Reaction equation

HRID 896309 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([CH2:28]OS(C)(=O)=O)=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:34])([CH3:3])[CH3:2].[C-:35]#[N:36].[K+]>CN(C=O)C>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([CH2:28][C:35]#[N:36])=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:34])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 20813972methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester

Product 1

HCID 22349407HCID 22349407, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester (16 mg, 0.033 mmol) and KCN (21 mg, 0.33 mmol) in DMF was stirred for 24 h at ambient temperature. The solvent was evaporated and the residue was purified by prep-HPLC (gradient 10%-100% B) to give 12 mg (88%) of [2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-yl]-acetonitrile as a colorless gum.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by prep-HPLC (gradient 10%-100% B)

Sources & evidence

ORD record
ord-39bbaee0e4314e6f81302b8d0c1dd2c3
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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