p-Toluenesulfonic acid → HCID 25120533, compound

HRID 1893466Notes

Reaction equation

HRID 1893466 reaction equation
C([NH:8][CH2:9][C:10]1[N:14]2[C:15]3[C:20]([N:21]=[C:22]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[C:13]2=[N:12][CH:11]=1)=[CH:19][C:18]([C:28]([F:31])([F:30])[F:29])=[CH:17][CH:16]=3)C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>CO.[Pd]>[NH2:8][CH2:9][C:10]1[N:14]2[C:15]3[C:20]([N:21]=[C:22]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[C:13]2=[N:12][CH:11]=1)=[CH:19][C:18]([C:28]([F:29])([F:31])[F:30])=[CH:17][CH:16]=3

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 25120534HCID 25120534, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 25120533HCID 25120533, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-({1-[(benzylamino)methyl]-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl}amino)propan-1-ol (23 mg, 0.05 mmol) in methanol (600 μL) were added 5% Pd/C (21 mg, 0.01 mmol) and para-toluenesulfonic acid (2 mg, 0.01 mmol). The mixture was stirred under one hydrogen atmosphere for 4 days at room temperature. The reaction mixture was filtered on Celite and rinsed with methanol and dichloromethane. The crude product was purified by preparative TLC (dichloromethane/methanol 9/1) to give the title compound (8 mg, 43%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered on Celite
  2. washrinsed with methanol and dichloromethane
  3. customThe crude product was purified by preparative TLC (dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-216fea84c96e4d1bbaf68acc5fc6b576
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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