Trifluoroacetic acid → HCID 54320219, compound

HRID 1783516Notes

Reaction equation

HRID 1783516 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[N:8]1[C:13]2=[N:14][C:15](S(C)=O)=[N:16][CH:17]=[C:12]2[CH2:11][NH:10][C:9]1=[O:21].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1.FC(F)(F)C(O)=O>C(#N)C.C(OCC)(=O)C>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[N:8]1[C:13]2=[N:14][C:15]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]4)=[CH:27][CH:28]=3)=[N:16][CH:17]=[C:12]2[CH2:11][NH:10][C:9]1=[O:21]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 68860079HCID 68860079, compound

Product 1

HCID 54320219HCID 54320219, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 300 mg (0.98 mmol) of 1-bicyclo[2.2.1]hept-2-yl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 374 mg (1.96 mmol) of 1-(4-aminophenyl)-4-methylpiperazine in 4.0 mL of acetonitrile is added 377 μL (4.90 mmol) of trifluoroacetic acid. The mixture is heated at 85° C. overnight. The cooled reaction mixture is diluted with ethyl acetate and washed two times with saturated aqueous sodium bicarbonate solution and once with brine. The organic phase is dried over magnesium sulfate and concentrated. The dark solid residue is triturated in 4 mL of 1:1 dichloromethane/ethyl acetate, filtered, washed with ethyl acetate, and dried to give 266 mg (63%) of the title compound: mp 251-254° C. (dec).

Workup

  1. customThe cooled reaction mixture
  2. washwashed two times with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe dark solid residue is triturated in 4 mL of 1:1 dichloromethane/ethyl acetate
  6. filtrationfiltered
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-b934ffe6a7bf40dfa66cbe5b680555f5
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

Loading…