反应详情

温度

0 °C

To a suspension of 4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyano-N-1,3-thiazol-4-ylbenzenesulfonamide, Example 809 (500 mg, 0.000797 mol) in methanol (4 mL) and dichloromethane (4 mL) was added triethylamine (161 mg, 0.00159 mol) and the reaction cooled to 0° C. in an ice/water bath. To the suspension was added sodium triacetoxyborohydride (422 mg, 0.00199 mol) and the reaction was then stirred at 0° C. for 10 minutes. Acetaldehyde (105 mg, 0.00239 mol) was added dropwise and the reaction stirred at 0° C. for 1.5 hours. The solvent was removed in vacuo to give an orange oil which was partitioned between dichloromethane (25 mL) and water (25 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL) and filtered through a phase separator. The solvent was removed in vacuo to give a pink solid which was triturated in hot ethyl acetate (10.0 mL), allowed to cool to room temperature and then filtered to give the title compound as a white solid, (431 mg).

1. stirringthe reaction stirred at 0° C. for 1.5 hours
2. customThe solvent was removed in vacuo
3. customto give an orange oil which
4. customwas partitioned between dichloromethane (25 mL) and water (25 mL)
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
7. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL)
8. filtrationfiltered through a phase separator
9. customThe solvent was removed in vacuo
10. customto give a pink solid which
11. customwas triturated in hot ethyl acetate (10.0 mL)
12. temperatureto cool to room temperature
13. filtrationfiltered