Trifluoroacetic acid → [5-(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1H-pyrazol-3-yl]-(4-fluoro-benzyl)-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[N:16](CC4C=CC(OC)=CC=4)[N:15]=[C:14]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:13]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[NH:16][N:15]=[C:14]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:13]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1Participants
3
Conditions
- Temperature
- 70 °C
Procedure
Into a round bottom flask, [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-(4-methoxy-benzyl)-1H-pyrazol-3-yl]-(4-fluoro-benzyl)-amine (149, 0.060 g, 0.13 mmol) was dissolved in 5 mL of trifluoroacetic acid (60 mmol) and the reaction was heated at 70° C. overnight. The reaction was cooled to room temperature, then concentrated under vacuum and ethyl acetate was added. This was washed with 1 M aqueous potassium carbonate and brine, dried with sodium sulfate and purified by silica gel column chromatography, eluting with 2-20% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum, and the solid further washed with ethyl acetate and hexane to provide the desired compound. 1H NMR was consistent with compound structure. MS (ESI) [M+H+]+=356.85.