Trifluoroacetic acid → HCID 71014413, compound

HRID 716062Notes

Reaction equation

HRID 716062 reaction equation
[CH3:1][C:2]([CH3:42])([CH3:41])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]=[C:22]([C:25]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[C:23]#[N:24])=[CH:17][CH:16]=3)[N:12]=2)[N:7](COCC[Si](C)(C)C)[CH:6]=1)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]([CH3:42])([CH3:41])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([CH:21]=[C:22]([C:25]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[C:23]#[N:24])=[CH:19][CH:20]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71014341HCID 71014341, compound

Product 1

HCID 71014413HCID 71014413, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 20 ml vial, 3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxymethyl)-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-2-(piperidine-1-carbonyl)prop-2-enenitrile (0.04 ml, 0.04 mmol) was dissolved in DCM (3 ml) and the reaction mixture was cooled to 0° C. TFA (2 ml, 0.0238 mole) was added drop wise at 0° C. and there reaction mixture was stirred for 3 h at room temperature. The solvent was evaporated and the residue was neutralized by NaHCO3 to pH 7-8 and the aq. layer was extracted with EtOAc. The organic layer was evaporated and the residue was dissolved in methanol. HCl and water were added and the solution was stirred at RT overnight and then neutralized with NaHCO3 to pH7-8. The crude product which precipitated was filtrated, washed with water and dried. The crude product was dissolved in a mixture of EtOAC and CH2Cl2, loaded on TLC plate and flashed with EtOAc:hexane=85:15 to yield 0.014 g of 3-[4-[[7-(2,2-dimethylpropanoyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]-2-(piperidine-1-carbonyl)prop-2-enenitrile.

Workup

  1. customthere reaction mixture
  2. customThe solvent was evaporated
  3. extractionthe aq. layer was extracted with EtOAc
  4. customThe organic layer was evaporated
  5. dissolutionthe residue was dissolved in methanol. HCl
  6. additionwater were added
  7. stirringthe solution was stirred at RT overnight
  8. customThe crude product which precipitated
  9. filtrationwas filtrated
  10. washwashed with water
  11. customdried
  12. dissolutionThe crude product was dissolved in a mixture of EtOAC and CH2Cl2

Sources & evidence

ORD record
ord-79ed8c7ac332454dbf2868aa37092898
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

Loading…