Trifluoroacetic acid → HCID 54755497, compound

HRID 2191584Notes

Reaction equation

HRID 2191584 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH:21]4[CH2:23][CH2:22]4)[N:19]=3)[N:14](COCC[Si](C)(C)C)[CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH:21]4[CH2:23][CH2:22]4)[N:19]=3)[NH:14][CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67001951HCID 67001951, compound

Product 1

HCID 54755497HCID 54755497, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-cyano-phenyl)-amide (113 mg, 0.26 mmol) in CH2Cl2 (2.6 mL) was added trifluoroacetic acid (1 mL). Stirred at room temperature for 2 h then neutralized with aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was dissolved in EtOH and NaOAc (0.7 g) was added. The reaction mixture was stirred at 60° C. overnight then cooled to room temperature and water and EtOAc were added. The aqueous layer was extracted with EtOAc and the combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (MeOH/CH2Cl2) to give 22 mg (28%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-cyano-phenyl)-amide. MS: (M+H)+=304; mp=272.0-274.0.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOH
  6. additionNaOAc (0.7 g) was added
  7. stirringThe reaction mixture was stirred at 60° C. overnight
  8. temperaturethen cooled to room temperature
  9. additionwater and EtOAc were added
  10. extractionThe aqueous layer was extracted with EtOAc
  11. washthe combined organics were washed with brine
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated
  14. customThe residue was purified by silica gel chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5a536e720ace4f0b9825494166a5a8d4
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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