HCID 178495906, compound → HCID 178495905, compound

HRID 1465819Notes

Reaction equation

HRID 1465819 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]([CH2:19][CH2:20][O:21][CH3:22])[CH3:18])=[CH:16][C:10]=3[N:9]=2)=[CH:4][C:3]=1[N+:23]([O-])=O>[Pd].C(OCC)(=O)C.CO>[CH3:22][O:21][CH2:20][CH2:19][N:17]([CH3:18])[C:15]1[CH:14]=[CH:13][C:11]2[NH:12][C:8]([C:5]3[CH:4]=[C:3]([NH2:23])[C:2]([NH2:1])=[CH:7][CH:6]=3)=[N:9][C:10]=2[CH:16]=1

Participants

4

Reactant 1

HCID 178495906HCID 178495906, compound

Product 1

HCID 178495905HCID 178495905, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of [2-(4-amino-3-nitro-phenyl)-1H-benzoimidazol-5-yl]-(2-methoxy-ethyl)-methyl-amine (0.65 g, 1.9 mmol) in 4:1 ethyl acetate/methanol (50 ml) under nitrogen, was added 5% palladium on carbon (100 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-[(2-methoxy-ethyl)-methyl-amino]-1H-benzoimidazol-2-yl}-benzene-1,2-diamine as a thick oil 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-1e9a7e8d210641039b4083e05fb15537
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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