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Imidazole → 4-[1-(2-Dimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-imidazol-1-yl-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

HRID 12291
Notes
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Reaction equation

HRID 12291 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:6]=[C:5](B(O)O)[CH:4]=[C:3]1[C:19]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])C)[C:22]2[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=2[N:20]=1.[NH:36]1[CH:40]=[CH:39][N:38]=[CH:37]1>N1C=CC=CC=1.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:30][SiH:28]([CH3:31])[CH2:27][CH2:26][O:25][CH2:24][N:23]1[C:22]2[CH:32]=[CH:33][CH:34]=[CH:35][C:21]=2[N:20]=[C:19]1[C:3]1[C:2](=[O:1])[N:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:14])([CH3:13])[CH3:15])[N:6]=[C:5]([N:36]2[CH:40]=[CH:39][N:38]=[CH:37]2)[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 795ImidazoleHCID 686797026-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid

Product 1

HCID 1317281464-[1-(2-Dimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-imidazol-1-yl-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalyst
HCID 962
Water
Solvent
HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

100 mg of 6-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid (example 55), 35.5 mg of copper(II) acetate and 20 mg of imidazole are dissolved in dry pyridine, and the solution is stirred at 80° C. for 3 hours. For workup, it is diluted with 20 ml of water and extracted several times with ethyl acetate, the organic phases are dried using a silica gel cartridge, and the volatile components are distilled off. The crude product is purified by preparative RP-HPLC (0-100% acetonitrile (+0.05% formic acid) in water (+0.05% formic acid)).

Workup

  1. extractionextracted several times with ethyl acetate
  2. customthe organic phases are dried
  3. distillationthe volatile components are distilled off
  4. customThe crude product is purified by preparative RP-HPLC (0-100% acetonitrile (+0.05% formic acid) in water (+0.05% formic acid))

Sources & evidence

ORD record
ord-0b1e3bb90b464aa88133a65f8742aa21
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07727989B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes