HCID 178448529, compound → HCID 178448528, compound

HRID 1465810Notes

Reaction equation

HRID 1465810 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:29]=[CH:28][C:14]3[NH:15][C:16]([C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([N+:25]([O-])=O)[CH:19]=4)=[N:17][C:13]=3[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]>[Pd].C(OCC)(=O)C.CO>[CH2:1]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:29]=[CH:28][C:14]3[NH:15][C:16]([C:18]4[CH:19]=[C:20]([NH2:25])[C:21]([NH2:24])=[CH:22][CH:23]=4)=[N:17][C:13]=3[CH:12]=2)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178448529HCID 178448529, compound

Product 1

HCID 178448528HCID 178448528, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 4-[5-(4-butyl-piperazin-1-yl)-1H-benzoimidazol-2-yl]-2-nitro-phenylamine (1.0 g, 2.5 mmol) in 4:1 ethyl acetate/methanol (100 ml) under nitrogen, was added 5% palladium on carbon (120 mg) and the mixture was first evacuated and then stirred at room temperature under an atmosphere of hydrogen for 1 day. The reaction mixture was then filtered through Celite, washed with 1:1 ethyl acetate/methanol (10 mL) and the combined filtrate and washings were concentrated to give the crude 4-[5-(4-butyl-piperazin-1-yl)-1H-benzoimidazol-2-yl]-benzene-1,2-diamine as an orange solid that was used in the next step without any purification.

Workup

  1. customthe mixture was first evacuated
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washwashed with 1:1 ethyl acetate/methanol (10 mL)
  4. concentrationthe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-5ea783a2cf0442f3a61b07cb6f4bd092
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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