HCID 58592783, compound → HCID 58592820, compound

HRID 642882Notes

Reaction equation

HRID 642882 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[N+:36]([O-])=O)[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=4)[NH:19][C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[N+]=[N-].[H][H]>[Pt].CO>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:20]2[NH:19][C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([N:11]4[CH2:10][CH2:9][N:8]([CH2:7][C:6]5[CH:5]=[C:4]([NH2:1])[C:35]([NH2:36])=[CH:34][CH:33]=5)[CH2:13][CH2:12]4)[C:22]=3[N:21]=2)=[CH:28][CH:27]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 58592783HCID 58592783, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58592820HCID 58592820, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

In a round bottom flask under nitrogen was combined 4-[4-(3-Azido-4-nitro-benzyl)-piperazin-1-yl]-2-(4-tert-butyl-phenyl)-1H-benzoimidazole (0.19 g, 0.37 mMol), methanol (20 mL), and 5% platinum on carbon (0.145 g, 0.037 mMol). A hydrogen balloon was attached, the flask evacuated, and a hydrogen atmosphere established. After stirring for four hours, the balloon was removed, the flask purged with nitrogen, and the reaction mixture filtered thru Celite with a large excess of methanol. The solution was concentrated to dryness on a rotary evaporator to yield 170 mg (100% yield) of 4-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-benzene-1,2-diamine as a brown oil. LC/MS (Method A), rt=0.90 mins., purity=85.9%, calculated mass=454, [M+H]+=455, [M−H]−=453.

Workup

  1. customIn a round bottom flask under nitrogen was combined
  2. customthe flask evacuated
  3. customthe balloon was removed
  4. customthe flask purged with nitrogen
  5. filtrationthe reaction mixture filtered thru Celite with a large excess of methanol
  6. concentrationThe solution was concentrated to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-5d42c42ad32a483f96363fb4a985c9dd
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

Loading…