Trifluoroacetic acid → 5-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione

HRID 716040Notes

Reaction equation

HRID 716040 reaction equation
[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:30]=[CH:29][C:20]([CH:21]=[C:22]4[S:26][C:25](=[O:27])[NH:24][C:23]4=[O:28])=[CH:19][CH:18]=3)[N:14]=2)[N:9](COCC[Si](C)(C)C)[CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:30]=[CH:29][C:20]([CH:21]=[C:22]4[S:26][C:25](=[O:27])[NH:24][C:23]4=[O:28])=[CH:19][CH:18]=3)[N:14]=2)[NH:9][CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867121265-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione

Product 1

HCID 780790635-(4-(7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dioneYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 35 ml vial, 5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione (0.100 g, 0.0001 mole) was taken in 8 ml CH2Cl2 and cooled to 0° C. under N2 atm. TFA (2 ml, 0.0268 mole) was added dropwise at 0° C. and the reaction mixture was stirred for 16 h at room temperature. After completion of the reaction, solvent was evaporated under reduced pressure from the reaction mixture and saturated NaHCO3 solution was added dropwise to make Ph basic. The solid that precipitated out was washed with water and pentane and 0.050 g of the solid was taken up in ethanol (20 ml) and NaOAc.3H2O (0.246 g, 0.0018 mole) was added. The reaction mixture was stirred at room temperature for 16 hr. Ethanol was evaporated under reduced pressure and the solid was washed with water and pentane. The crude compound was purified by triturating with pentane to yield 0.018 g of the title compound.

Workup

  1. customAfter completion of the reaction, solvent
  2. customwas evaporated under reduced pressure from the reaction mixture and saturated NaHCO3 solution
  3. additionwas added dropwise
  4. customThe solid that precipitated out
  5. washwas washed with water and pentane and 0.050 g of the solid
  6. stirringThe reaction mixture was stirred at room temperature for 16 hr
  7. customEthanol was evaporated under reduced pressure
  8. washthe solid was washed with water and pentane
  9. customThe crude compound was purified
  10. customby triturating with pentane

Sources & evidence

ORD record
ord-b785be4c5ffc403b8575f8758ea2faad
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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