Trifluoroacetic anhydride → HCID 66987515, compound

HRID 555723Notes

Reaction equation

HRID 555723 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3[N:15]([CH2:25][CH2:26]C(C)(C)C)[CH:16]=[N:17][C:18]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:7]([C:11]([NH2:13])=O)[NH:8]2)=[CH:4][CH:3]=1.C(O[C:38]([C:40](F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3[N:15]([CH2:25][C:26]4[CH:40]=[CH:38][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH:16]=[N:17][C:18]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:7]([C:11]#[N:13])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 66987575HCID 66987575, compound

Product 1

HCID 66987515HCID 66987515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 138 (150 mg, 0.33 mmol) and TFAA (1.5 mL) in DCM (1.5 mL) is heated to reflux. After completion the reaction mixture is quenched by saturated aqueous NaHCO3. DCM is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; ES-MS: M+H=444.9: AtRet=4.44.

Workup

  1. customAfter completion the reaction mixture is quenched by saturated aqueous NaHCO3
  2. additionDCM is added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3295a754807e4213a7a733bcf2779a72
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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