HCID 178507431, compound → HCID 178507430, compound

HRID 1465814Notes

Reaction equation

HRID 1465814 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][C:17]([N:19]4[CH2:24][CH2:23][S:22][CH2:21][CH2:20]4)=[CH:18][C:12]=3[N:11]=2)[CH:7]=[CH:6][C:5]=1[NH2:25])([O-])=O>[Pd].C(OCC)(=O)C.CO>[N:19]1([C:17]2[CH:16]=[CH:15][C:13]3[NH:14][C:10]([C:8]4[CH:9]=[C:4]([NH2:1])[C:5]([NH2:25])=[CH:6][CH:7]=4)=[N:11][C:12]=3[CH:18]=2)[CH2:20][CH2:21][S:22][CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 178507431HCID 178507431, compound

Product 1

HCID 178507430HCID 178507430, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-nitro-4-(5-thiomorpholin-4-yl-1H-benzoimidazol-2-yl)-phenylamine (1.0 g, 2.8 mmol) in 4:1 ethyl acetate/methanol (80 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-(5-thiomorpholin-4-yl-1H-benzoimidazol-2-yl)-benzene-1,2-diamine as a red 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-bb49c88a26754948ba9545ff7afd7c87
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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