6-[[3-[(3,4-Dimethylphenyl)amino]-4,6-dinitrophenyl]oxy]hexanoic acid methyl ester → 6-[(5-Amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

HRID 2054669Notes

Reaction equation

HRID 2054669 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][C:13]([N+:19]([O-])=O)=[C:12]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=2)[CH:11]=1.Cl.[C:33](=N)(O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CO>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([NH2:16])=[CH:14][C:13]2[N:19]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:22]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=3)[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 866047786-[[3-[(3,4-Dimethylphenyl)amino]-4,6-dinitrophenyl]oxy]hexanoic acid methyl esterHCID 178479544HCID 178479544, compound

Product 1

HCID 673647576-[(5-Amino-1-(3,4-dimethylphenyl)-2-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.45 g of 6-[[3-[(3,4-dimethylphenyl)amino]-4,6-dinitrophenyl]oxy]hexanoic acid methyl ester was hydrogenated in methanol according to general operating instructions 1. 500 mg of the crude product was reacted with benzimidate hydrochloride according to general operating instructions 4. Contrary to general operating instructions 4, after being taken up in solvent, the crude product was not washed with aqueous hydrochloric acid.

Workup

  1. washthe crude product was not washed with aqueous hydrochloric acid

Sources & evidence

ORD record
ord-87420b0ffb61440abcfaa37710e2209a
Source dataset
uspto-grants-2008_02
Patent number
US07329679B2

Reaction notes

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