反应详情

温度

0 °C

Add a solution of borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran; 3.8 mL, 3.8 mmol) to a 0° C. solution of (S)-2-fluoro-1-[2-(2-methoxy-ethyl)-4-(2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulen-10-yl)-piperazin-1-yl]-ethanone (0.18 g, 0.38 mmol) in anhydrous tetrahydrofuran (3 mL) and stir at 0° C. for 3 hours. Quench the reaction, in an ice/water bath, slowly with methanol. Concentrate the reaction under reduced pressure and reconstitute in anhydrous dichloroethane (6 mL). Add ethylenediamine (0.23 mL, 3.4 mmol) and reflux for 45 minutes. Cool the reaction to ambient temperature and dilute with deionized water and dichloromethane (20 mL each). Separate the organic layer and extract the aqueous layer with dichloromethane (2×). Wash the combined organics with deionized water and then a saturated solution of sodium chloride, and then dry (sodium sulfate), filter, and concentrate under reduced pressure to an orange oil (0.19 g). Purify the oil by flash chromatography, eluting with a gradient of a solution of ethyl acetate:hexane (1:1, 0-50% in hexane over 45 minutes, then 100% for 13 minutes) to give the title compound: 0.050 g (29%). Mass spectrum (APCI+, m/e): 458 (M+1).

1. customQuench
2. customthe reaction
3. concentrationConcentrate
4. customthe reaction under reduced pressure and reconstitute in anhydrous dichloroethane (6 mL)
5. temperatureCool
6. customthe reaction to ambient temperature
7. customSeparate the organic layer
8. extractionextract the aqueous layer with dichloromethane (2×)
9. washWash the combined organics with deionized water
10. dry with materiala saturated solution of sodium chloride, and then dry (sodium sulfate)
11. filtrationfilter
12. concentrationconcentrate under reduced pressure to an orange oil (0.19 g)
13. customPurify the oil by flash chromatography
14. washeluting with a gradient of a solution of ethyl acetate:hexane (1:1, 0-50% in hexane over 45 minutes