Trifluoroacetic anhydride → HCID 71515734, compound

HRID 2277751Notes

Reaction equation

HRID 2277751 reaction equation
[CH2:1]([S:3](=[N:29]C#N)([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[O:26][CH3:27])[C:16]([F:28])=[CH:15][N:14]=2)[CH:7]=1)=[O:4])[CH3:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(OCC)(=O)C.C1COCC1>[CH2:1]([S:3]([CH2:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[O:26][CH3:27])[C:16]([F:28])=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)(=[NH:29])=[O:4])[CH3:2]

Participants

7

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 71515733HCID 71515733, compound

Product 1

HCID 71515734HCID 71515734, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of (rac)-[ethyl(3-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidin-2-yl]-amino}benzyl)oxido-λ6-sulfanylidene]cyanamide (230 mg; 0.52 mmol) in DCM (23.1 mL) at 0° C., TFAA (0.55 mL; 3.89 mmol) was added. The mixture was allowed to react at RT for 2 hours. The reaction mixture was concentrated, taken up in MeOH (3.6 mL) and treated with potassium carbonate (358 mg; 2.58 mmol). The mixture was allowed to react at RT for 2 hours. The reaction mixture was diluted with ethyl acetate and THF and washed with saturated aqueous sodium chloride solution. The organic phase was filtered using a Whatman filter and concentrated. The residue was purified by chromatography (DCM/EtOH 4:1).

Workup

  1. customto react at RT for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto react at RT for 2 hours
  4. washwashed with saturated aqueous sodium chloride solution
  5. filtrationThe organic phase was filtered
  6. filtrationfilter
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (DCM/EtOH 4:1)

Sources & evidence

ORD record
ord-dc62de2c8d4142ff8e1f6758eba199af
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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