HCID 11481734, compound → HCID 9871847, compound

HRID 277704Notes

Reaction equation

HRID 277704 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:25]1[CH2:33][NH:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38]>ClCCl>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:3]=1[C:4]([N:34]([CH2:33][C:25]1[N:24]([CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=1)[CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])=[O:5]

Participants

4

Reactant 2

HCID 11481734HCID 11481734, compoundHCID 53702815HCID 53702815, compound

Product 1

HCID 9871847HCID 9871847, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.4 mmole 1-{[2-(chloromethyl)-benzimidazolyl]methyl}-2-methoxybenzene in 20 mL of dryacetonitrile is treated with 10 mL of isoamylamine for 16 hours at room temperature. The solvent is removed in vacuo and the residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH. The ethyl acetate layer is dried over anhydrous Na2SO4 and solvent removed in vacuo to afford 1.7 g 97% ({1-[(2-methoxyphenyl)methyl]benzimidazol-2-yl}methyl)(3-methylbutyl) amine. 2-Chloro-3,4-dimethoxybenzoylchloride (1.5 equ.) is treated with 1.0 equivalent of ({1-[(2-methoxyphenyl)methyl]benzimidazol-2-yl}methyl)(3-methylbutyl) amine in dichloromethane at room temperature for 1 hour. The reaction is quenched with 1 N NaOH and partitioned between dichloromethane and water. The organic layer is dried with Na2SO4 and the solvent removed in vacuo. The residue is chromatographed (SiO2) with ethyl acetate to afford 95% of (2-chloro-3,4-dimethoxyphenyl)-N-({1-[(2-methoxyphenyl)methyl]benzimidazol-2-yl}methyl)-N-(3-methylbutyl)carboxamide (Compound 1). Mass Spec M+ 537.

Workup

  1. customThe reaction is quenched with 1 N NaOH
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layer is dried with Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue is chromatographed (SiO2) with ethyl acetate

Sources & evidence

ORD record
ord-c718ea203ec34a82ba99642a4376fc2e
Source dataset
uspto-grants-2002_03
Patent number
US06358949B1

Reaction notes

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