Trifluoroacetic acid → 4-Prop-2-ynyl-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one

HRID 1433003Notes

Reaction equation

HRID 1433003 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]#[CH:26])[CH2:20][C:19]1=[O:27])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:24]([N:21]1[CH2:22][CH2:23][N:18]([CH2:17][C:9]2[NH:8][C:16]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[CH:10]=2)[C:19](=[O:27])[CH2:20]1)[C:25]#[CH:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53990821HCID 53990821, compound

Product 1

HCID 544090924-Prop-2-ynyl-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 2-(2-oxo-4-prop-2-ynyl-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (1.3 g, 3.53 mmol) in CH2Cl2 (100 mL) is added TFA (20 mL) at 0° C. After 6 h, the reaction mixture is concentrated to dryness and then partitioned between aqueous NaHCO3 (500 mL) and CH2Cl2 (200 mL) and the layers are separated. The aqueous phase is extracted four times with CH2Cl2 (100 mL) and the combined organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue is purified by flash silica gel chromatography (CH2Cl2 to 10% MeOH/CH2Cl2) to provide 616 mg (65%) of the title compound as a pale yellow solid.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness
  2. custompartitioned between aqueous NaHCO3 (500 mL) and CH2Cl2 (200 mL)
  3. customthe layers are separated
  4. extractionThe aqueous phase is extracted four times with CH2Cl2 (100 mL)
  5. washthe combined organic phase is washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue is purified by flash silica gel chromatography (CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c8292295a71d4e289bfffadf1ab9a8d6
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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