Ferrostatin-1 → Ethyl 1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate

HRID 2216695

Reaction equation

HRID 2216695 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[OH:21][C:22]1[CH:31]=[CH:30][C:25]([C:26](=N)OC)=[CH:24][CH:23]=1>CO>[CH:14]1([N:13]2[C:12]3[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=3[N:1]=[C:26]2[C:25]2[CH:30]=[CH:31][C:22]([OH:21])=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 4068248Ferrostatin-1HCID 135889529Methyl 4-hydroxybenzimidate hydrochloride

Product 1

HCID 135486203Ethyl 1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylateYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-amino-4-cyclohexylaminobenzoate (130 g) obtained in Example 1, Step 3, and methyl 4-hydroxybenzimidate hydrochloride (139 g) were added to methyl alcohol (1500 ml), and the mixture was refluxed under heating for 4 hr. The reaction mixture was allowed to cool and the precipitated crystals were collected by filtration to give the title compound (131 g, yield 72%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hr
  3. temperatureto cool
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-902b03e2d48c489aa5e3721e4c8ab64f
Source dataset
uspto-grants-2006_09
Patent number
US07112600B1

Linked notes

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