Trifluoroacetic acid → HCID 71014324, compound

HRID 716067Notes

Reaction equation

HRID 716067 reaction equation
[C:1]([C:3](=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[N:28]=[C:29]3[C:35]([C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:34][N:33](COCC[Si](C)(C)C)[C:30]3=[N:31][CH:32]=2)=[CH:22][CH:21]=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:5])#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:6]1([C:4]([C:3](=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]3[N:28]=[C:29]4[C:35]([C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:34][NH:33][C:30]4=[N:31][CH:32]=3)=[CH:22][CH:21]=2)[C:1]#[N:2])=[O:5])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71014294HCID 71014294, compound

Product 1

HCID 71014324HCID 71014324, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-[2-cyano-3-[4-[[7-(2,2-dimethylpropanoyl)-5-(2-trimethylsilylethoxy-methyl)-pyrrolo[2,3-b]pyrazin-2-yl]amino]phenyl]prop-2-enoyl]piperazine-1-carboxylate (80 mg, 0.12 mmol) was dissolved in DCM (3 mL), cooled in an ice bath, and TFA (3 mL, 0.12 mmol) was added. The reaction mixture was stirred overnight, and then most of the solvent was removed in vacuo. The mixture was neutralized by Na2HCO3 to pH 7-8, extracted by EtOAc, combined organic layer was evaporated. The residue was dissolved in methanol (15 mL), adding HCl (0.05 mL, 0.12 mmol, and a few of drops water, and the mixtured was stirred overnight. When the reaction was deemed complete by LCMS analysis, the solvent was removed, and the product precipitated from EtOAc/MeOH to get 21 mg of 2-(piperazine-1-carbonyl)-3-(4-((7-pivaloyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)phenyl)acrylonitrile.

Workup

  1. temperaturecooled in an ice bath
  2. custommost of the solvent was removed in vacuo
  3. extractionextracted by EtOAc
  4. customwas evaporated
  5. dissolutionThe residue was dissolved in methanol (15 mL)
  6. additionadding HCl (0.05 mL, 0.12 mmol
  7. stirringa few of drops water, and the mixtured was stirred overnight
  8. customthe solvent was removed
  9. customthe product precipitated from EtOAc/MeOH

Sources & evidence

ORD record
ord-d76e8be4514f4fc6ac3a936b6bdb49e7
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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