HCID 178495856, compound → HCID 178495855, compound

HRID 1465812Notes

Reaction equation

HRID 1465812 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]([NH:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:16][C:10]=3[N:9]=2)=[CH:4][C:3]=1[N+:22]([O-])=O>[Pd].C(OCC)(=O)C.CO>[CH3:21][O:20][CH2:19][CH2:18][NH:17][C:15]1[CH:14]=[CH:13][C:11]2[NH:12][C:8]([C:5]3[CH:4]=[C:3]([NH2:22])[C:2]([NH2:1])=[CH:7][CH:6]=3)=[N:9][C:10]=2[CH:16]=1

Participants

4

Reactant 1

HCID 178495856HCID 178495856, compound

Product 1

HCID 178495855HCID 178495855, 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)-amine (0.5 g, 1.5 mmol) in 4:1 ethyl acetate/methanol (50 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-(2-methoxy-ethylamino)-1H-benzoimidazol-2-yl]-benzene-1,2-diamine which 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-3dee840ecca34593817cc476badcd402
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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