Thionyl Chloride → {(S)-1-Methyl-2-[7-(4-pyridin-2-yl-piperazin-1-ylmethyl)-furo[2,3-g]indazol-1-yl]-ethyl}-carbamic acid benzyl ester

A solution of the product from Example 3, Step B (0.18 g, 0.475 mmol) in dichloromethane (20 mL) was cooled (ice bath) and thionyl chloride (0.052 mL, 0.71 mmol) added. The mixture was stirred for 30 min and then evaporated to a residue which was dissolved in dichloromethane (20 mL); this solution was evaporated and the residue dried under a vacuum. The residue was dissolved in dichloromethane (20 mL) and 1-(2-pyridyl)piperazine (0.5 mL, 3.4 mmol) was added, and the mixture was stirred at room temperature for one hour at which point additional 1-(2-pyridyl)piperazine (0.9 mL) was added. Solvent was removed by evaporation (45° C.) and THF (10 mL) was added, followed by heating the mixture at reflux temperature for one hour. This reaction mixture was evaporated and the residue dissolved in methanol (25 mL) and triethylamine (1.5 mL) followed by evaporation of this mixture to a residue which was purified by chromatography (silica gel, hexane/ethyl acetate) to give a foamy solid (0.21 g, 84%): LC/MS m/z 525 [M+H]+.

1. additionadded
2. customevaporated to a residue which
3. dissolutionwas dissolved in dichloromethane (20 mL)
4. customthis solution was evaporated
5. customthe residue dried under a vacuum
6. dissolutionThe residue was dissolved in dichloromethane (20 mL)
7. additionwas added
8. customSolvent was removed by evaporation (45° C.) and THF (10 mL)
9. additionwas added
10. temperatureby heating the mixture
11. temperatureat reflux temperature for one hour
12. customThis reaction mixture was evaporated
13. dissolutionthe residue dissolved in methanol (25 mL)
14. customtriethylamine (1.5 mL) followed by evaporation of this mixture to a residue which
15. customwas purified by chromatography (silica gel, hexane/ethyl acetate)

ORDレコード

ord-26fcc997a8fe44ebb9139b2af8f17c1c

出典データセット

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07476687B2