HCID 178456330, compound → HCID 178456329, compound

HRID 1465808Notes

Reaction equation

HRID 1465808 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:28]=[CH:27][C:13]3[NH:14][C:15]([C:17]4[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([N+:24]([O-])=O)[CH:18]=4)=[N:16][C:12]=3[CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C.CO>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:28]=[CH:27][C:13]3[NH:14][C:15]([C:17]4[CH:18]=[C:19]([NH2:24])[C:20]([NH2:23])=[CH:21][CH:22]=4)=[N:16][C:12]=3[CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 178456330HCID 178456330, compound

Product 1

HCID 178456329HCID 178456329, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 4-[5-(4-isopropyl-piperazin-1-yl)-1H-benzoimidazol-2-yl]-2-nitro-phenylamine (500 mg, 1.3 mmol) in 4:1 ethyl acetate/methanol (50 ml) 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 filtered through Celite, washed with methanol, and the combined filtrate and washings were concentrated to give the crude 4-[5-(4-isopropyl-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 filtered through Celite
  3. washwashed with methanol
  4. concentrationthe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-2ac375f0fb0f4dffa65b78b3a990222b
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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