Iodide Ion → Diisopropylether methanol

HRID 1786243Notes

Reaction equation

HRID 1786243 reaction equation
BrC1C=CC(N2[C:12](C[N+](C)(C)C)=[C:11]([CH3:18])N=C2)=C(C#N)C=1.[I-].[O:22]=[C:23]1[CH:28]=CN(CC(NN)=O)C=[CH:24]1>>[CH3:23][OH:22].[CH:23]([O:22][CH:11]([CH3:12])[CH3:18])([CH3:28])[CH3:24]

Participants

4

Reactant 3

HCID 30165Iodide IonHCID 63577462(4-oxo-4H-pyridin-1-yl)-acetic acid hydrazideHCID 86611792[3-(4-bromo-2-cyano-phenyl)-5-methyl-3H-imidazol-4-ylmethyl]-trimethyl-ammonium

Product 1

HCID 21882575Diisopropylether methanol

Procedure

As described for example 84d, [3-(4-bromo-2-cyano-phenyl)-5-methyl-3H-imidazol-4-ylmethyl]-trimethyl-ammonium; iodide (example 84c) was reacted with (4-oxo-4H-pyridin-1-yl)-acetic acid hydrazide. After evaporation of the solvent the residue was concentrated and chromatographed (SiO2, dichloromethane:methanol=100:0 to 92:8). Trituration with methanol/diisopropylether afforded the title compound as an off-white solid (yield: 33%). MS: m/e=425.0/423.0 [M+H]+.

Workup

  1. customAfter evaporation of the solvent the residue
  2. concentrationwas concentrated
  3. customchromatographed (SiO2, dichloromethane:methanol=100:0 to 92:8)

Sources & evidence

ORD record
ord-609e140f7df14979a2f7e483e38df976
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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