Trifluoroacetic acid → 2-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide

HRID 716064Notes

Reaction equation

HRID 716064 reaction equation
[C:1]([C:3](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][N:23](COCC[Si](C)(C)C)[C:20]3=[N:21][CH:22]=2)=[CH:12][CH:11]=1)[C:4]([NH:6][CH2:7][CH3:8])=[O:5])#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3](=[CH:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][NH:23][C:20]3=[N:21][CH:22]=2)=[CH:14][CH:15]=1)[C:4]([NH:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 779816092-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide

Product 1

HCID 710142262-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml vial 2-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxy-methyl)-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide (37 mg, 0.07 mmol was dissolved in DCM (3 ml) and TFA (2.63 ml, 18.88 mmol) was added. The reaction mixture was stirred at room temperature for 3 hr. The solvent was evaporated, the residue was neutralized with NaHCO3 to pH 7-8 and the aq. layer was extracted with EtOAc. The solvent was evaporated and the residue was dissolved in methanol (5 ml). HCl (4 drops) and water, were added and the reaction mixture was stirred at RT overnight. The reaction was neutralized with NaHCO3 to pH 7-8. The product was precipitated, filtrated and washed by water to yield 20 mg 2-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-N-ethyl-prop-2-enamide as dark red brown solid.

Workup

  1. customThe solvent was evaporated
  2. extractionthe aq. layer was extracted with EtOAc
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in methanol (5 ml)
  5. additionHCl (4 drops) and water, were added
  6. stirringthe reaction mixture was stirred at RT overnight
  7. customThe product was precipitated
  8. filtrationfiltrated
  9. washwashed by water

Sources & evidence

ORD record
ord-168f442ba44a4156a20c0442fd930a44
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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