Acetic Acid → HCID 22662668, compound

To a solution of 5-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo)[2,3-b]pyridin-5-yl]-pyridine-3-carbaldehyde (24 mg, 0.050 mmol) and dimethyl-(2-piperazin-1-yl-ethyl)-amine (10 μL, 0.065 mmol) in 1.5 ml dichloroethane was added 3 μL of AcOH. The mixture was stirred at room temperature for 30 minutes before sodium trioxyucetylborohydride (22 mg, 0.1 mmol) was added. The reaction mixture was stirred at room temperature for another 2 hours before being concentrated. The resulting residue was then dissolved in 2 ml of MeOH, to this was added 1.00 μL, of 5N NaOH, the mixture was stirred at 60° C. for 2 hours. Solvents were removed and the residue was purified by flash silica gel chromatography using ethyl acetate and then a solvent mixture (NH4OH/MeOH/CH2Cl2/EtOAc=0.05/1/4/4) to afford (2-(4-{5-[3-(2-Methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl-pyridin-3-yl}-piperazin-1-yl)-ethyl]-dimethyl-amine (4.70 mg, 20% yield) as a white solid. MS: m/z 471 [MH+].

1. additionwas added
2. concentrationbefore being concentrated
3. dissolutionThe resulting residue was then dissolved in 2 ml of MeOH
4. additionto this was added 1.00 μL
5. stirringof 5N NaOH, the mixture was stirred at 60° C. for 2 hours
6. customSolvents were removed
7. customthe residue was purified by flash silica gel chromatography

ORD record

ord-02bfae8553d640e1aff489f2509c575c

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906648B2