Trifluoroacetic acid → 4-Prop-2-ynyl-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-piperazin-2-one
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
Product 1
Reagents, catalysts & solvents 1
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.