(5-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-2-nitro-phenyl)-pyridin-3-ylmethyl-amine → HCID 58592716, compound

HRID 642885Notes

Reaction equation

HRID 642885 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:28]=[CH:29][C:30]([N+:41]([O-])=O)=[C:31]([NH:33][CH2:34][C:35]6[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=6)[CH:32]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:32]=[C:31]([NH:33][CH2:34][C:35]6[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=6)[C:30]([NH2:41])=[CH:29][CH:28]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58592806(5-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-2-nitro-phenyl)-pyridin-3-ylmethyl-amine

Product 1

HCID 58592716HCID 58592716, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (5-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-2-nitro-phenyl)-pyridin-3-ylmethyl-amine (0.05 g, 0.087 mMol) in methanol (10 mL) under nitrogen was added platinum on carbon (0.034g, 0.0087 mMol) and the reaction mixture evacuated. A hydrogen filled balloon was attached and the mixture stirred under a hydrogen atmosphere for two hours. The balloon was removed, the flask purged with nitrogen, and the mixture filtered thru Celite with a large excess of methanol. The resulting solution was concentrated to dryness on a rotory evaporator to yield 4-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-N2-pyridin-3-ylmethyl-benzene-1,2-diamine as a crude oil (0.047 g, 100% yield). LC/MS (Method A), rt=0.86 mins., purity=68%, calculated mass=545, [M+H]+=546, [M−H]−=544.

Workup

  1. customthe reaction mixture evacuated
  2. customThe balloon was removed
  3. customthe flask purged with nitrogen
  4. filtrationthe mixture filtered
  5. concentrationThe resulting solution was concentrated to dryness on a rotory evaporator

Sources & evidence

ORD record
ord-40f8ce9a161f468596085ec1a12767c3
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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