4-Chloro-2-methoxy-6-methylaniline → N2-(4-Chloro-2-methoxy-6-methylphenyl)-N7-(4-chlorophenyl)-N7-isopropyl-1-methyl-1H-benzimidazole-2,7-diamine Hydrochloride

HRID 2235557Notes

Reaction equation

HRID 2235557 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([N:12]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH:13]([CH3:15])[CH3:14])=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Cl:23][C:24]1[CH:30]=[C:29]([CH3:31])[C:27]([NH2:28])=[C:26]([O:32][CH3:33])[CH:25]=1>C(OCC)(=O)C>[ClH:1].[Cl:23][C:24]1[CH:30]=[C:29]([CH3:31])[C:27]([NH:28][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([N:12]([C:16]4[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=4)[CH:13]([CH3:14])[CH3:15])=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:26]([O:32][CH3:33])[CH:25]=1

Participants

4

Reactant 2

HCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 685826702-chloro-N-(4-chlorophenyl)-N-isopropyl-1-methyl-1H-benzimidazol-7-amine

Product 1

HCID 86613000N2-(4-Chloro-2-methoxy-6-methylphenyl)-N7-(4-chlorophenyl)-N7-isopropyl-1-methyl-1H-benzimidazole-2,7-diamine HydrochlorideYield 19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-N-(4-chlorophenyl)-N-isopropyl-1-methyl-1H-benzimidazol-7-amine (30 mg, 0.90 mmol) and 4-chloro-2-methoxy-6-methylaniline (46 mg, 0.27 mmol) was stirred at 120° C. for 19 h. The mixture was dissolved in ethyl acetate (30 ml), washed with saturated aqueous sodium bicarbonate (15 ml) and water (10 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by reverse phase HPLC (acetonitrile containing 0.1 trifluoroacetic acid/water containing 0.1% trifluoroacetic acid). The fraction was concentrated to dryness, dissolved in methanol (10 ml) and treated with 2 M hydrogen chloride in diethyl ether (2 ml) and evaporated in vacuo to give 7.8 mg (19%) of the title compound as a powder.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (15 ml) and water (10 ml)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by reverse phase HPLC (acetonitrile containing 0.1 trifluoroacetic acid/water containing 0.1% trifluoroacetic acid)
  5. concentrationThe fraction was concentrated to dryness
  6. dissolutiondissolved in methanol (10 ml)
  7. additiontreated with 2 M hydrogen chloride in diethyl ether (2 ml)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-675ef35b7d1f4a20978203754019c576
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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