HCID 178507429, compound → HCID 178507428, compound

HRID 1465825Notes

Reaction equation

HRID 1465825 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]4)=[CH:16][C:10]=3[N:9]=2)=[CH:4][C:3]=1[N+:26]([O-])=O>[Pd].C(OCC)(=O)C.CO>[NH2:26][C:3]1[CH:4]=[C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([N:17]4[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]4)=[CH:16][C:10]=3[N:9]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 178507429HCID 178507429, compound

Product 1

HCID 178507428HCID 178507428, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-{4-[2-(4-amino-3-nitro-phenyl)-1H-benzoimidazol-5-yl]-piperazin-1-yl}-ethanol (1.0 g, 2.6 mmol) in 4:1 ethyl acetate/methanol (100 ml) under nitrogen, was added 5% palladium on carbon (200 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 2-{4-[2-(3,4-diamino-phenyl)-1H-benzoimidazol-5-yl]-piperazin-1-yl}-ethanol as a reddish 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-9dfe18cc67d84aa49fd1a0e0954a001f
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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