Trifluoroacetic acid → HCID 54308876, compound

HRID 1783514Notes

Reaction equation

HRID 1783514 reaction equation
[CH:1]([N:4]1[C:9]2=[N:10][C:11](S(C)=O)=[N:12][CH:13]=[C:8]2[CH2:7][NH:6][C:5]1=[O:17])([CH3:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.FC(F)(F)C(O)=O>C(#N)C>[CH:1]([N:4]1[C:9]2=[N:10][C:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[CH:23][CH:24]=3)=[N:12][CH:13]=[C:8]2[CH2:7][NH:6][C:5]1=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 54030904HCID 54030904, compound

Product 1

HCID 54308876HCID 54308876, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Prepared from 400 mg (1.57 mmol) of 1-isopropyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 600 mg (3.14 mmol) of 1-(4-aminophenyl)-4-methylpiperazine and 605 μL (7.85 mmol) of trifluoroacetic acid in 6.4 mL of acetonitrile. The reaction mixture is heated at 85° C. for 48 hours. After the workup, the crude residue is triturated in ethyl acetate/dichloromethane and filtered. The solids are redissolved in dichloromethane, and the solvent is evaporated under a flow of nitrogen while ethyl acetate is added to maintain a volume of 5 mL. The suspension is filtered, and the solids are washed with ethyl acetate/dichloromethane, and dried to give 470 mg (78%) of the title compound:

Workup

  1. customAfter the workup, the crude residue is triturated in ethyl acetate/dichloromethane
  2. filtrationfiltered
  3. dissolutionThe solids are redissolved in dichloromethane
  4. customthe solvent is evaporated under a flow of nitrogen while ethyl acetate
  5. additionis added
  6. temperatureto maintain a volume of 5 mL
  7. filtrationThe suspension is filtered
  8. washthe solids are washed with ethyl acetate/dichloromethane
  9. customdried

Sources & evidence

ORD record
ord-8f8ef3d2b78644d881d49baf3b0135de
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

Loading…