Trifluoroacetic acid → HCID 178486806, compound

HRID 1993349Notes

Reaction equation

HRID 1993349 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](=[O:31])[N:24]([CH3:30])[C:25](SC)=[N:26][CH:27]=2)=[CH:18][C:17]=1[F:32].C(O)(C(F)(F)F)=[O:34].OO.NC(N)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>CC#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](=[O:31])[N:24]([CH3:30])[C:25]([OH:34])=[N:26][CH:27]=2)=[CH:18][C:17]=1[F:32]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 11858026HCID 11858026, compound

Product 1

HCID 178486806HCID 178486806, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one (Step 1, 1.048 g, 2.3 mmol) was dissolved in CH3CN (15 mL) and TFA (1.7 mL) and cooled to 0° C. Urea hydrogen peroxide (290 mg, 3.09 mmol) was added, and the reaction was stirred for 5 min. trifluoroacetic anhydride (0.43 mL, 3.09 mmol) was added, and the reaction was warmed to RT and stirred for 40 min. The mixture was quenched with H2O (10 mL) and EtOAc (25 mL) and allowed to stand overnight. Saturated NaHCO3 (10 mL) and EtOAc were added, and the layers were separated. The aqueous layer was extracted with EtOAc, and the organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified on silica gel (EtOAc→1:1 EtOAc/MeOH) to give title compound. MS (ESI pos. ion) m/z: 411. Calc'd for C21H17FN3O5: 410.39.

Workup

  1. additionwas added
  2. customThe mixture was quenched with H2O (10 mL) and EtOAc (25 mL)
  3. waitto stand overnight
  4. additionSaturated NaHCO3 (10 mL) and EtOAc were added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on silica gel (EtOAc→1:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-a0fcd48c6bc340a4a98bde8db0a0b806
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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