HCID 178507435, compound → HCID 178507434, compound

HRID 1465827Notes

Reaction equation

HRID 1465827 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][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:16][C:10]=3[N:9]=2)=[CH:4][C:3]=1[N+:24]([O-])=O>[Pd].C(OCC)(=O)C.CO>[N:18]1([NH:17][C:15]2[CH:14]=[CH:13][C:11]3[NH:12][C:8]([C:5]4[CH:4]=[C:3]([NH2:24])[C:2]([NH2:1])=[CH:7][CH:6]=4)=[N:9][C:10]=3[CH:16]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 178507435HCID 178507435, compound

Product 1

HCID 178507434HCID 178507434, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of [2-(4-amino-3-nitro-phenyl)-1H-benzoimidazol-5-yl]-morpholin-4-yl-amine (0.5 g, 1.4 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-(morpholin-4-ylamino)-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-207ac59a6fec402b9a922072aa6b5fb5
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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