HCID 178484673, compound → HCID 178484672, compound

HRID 1465817Notes

Reaction equation

HRID 1465817 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([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)=[O:4]>[Pd].C(OCC)(=O)C.CO>[CH3:1][N:2]([CH3:30])[C:3]([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:23]=[CH:22][C:21]([NH2:24])=[C:20]([NH2:25])[CH:19]=4)=[N:17][C:13]=3[CH:12]=2)[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 1

HCID 178484673HCID 178484673, compound

Product 1

HCID 178484672HCID 178484672, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 4-[2-(4-amino-3-nitro-phenyl)-1H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid dimethylamide (1.0 g, 2.4 mmol) in 4:1 ethyl acetate/methanol (100 ml) under nitrogen, was added 5% palladium on carbon (240 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-[2-(3,4-diamino-phenyl)-1H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid dimethylamide 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-cbc25a781b4a471f8e7a34fdf3118722
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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