Ethylenediamine → HCID 68702989, compound

Temperature

100 °C

A mixture of 2,4,6-trimethylbenzenesulfonic acid 3-(4-chlorophenyl)-8-formyl-2-isopropyl-4-oxo-4H-chromen-7-yl ester (141 mg, 0.269 mmol) and ethylene diamine (0.6 ml) in anhydrous pyridine (3.5 ml) in a sealed 5 ml microwave tube is heated under microwave irradiation at 100° C. for 1 h. A further aliquot of ethylene diamine (0.6 ml) is added, and the mixture is heated at 140° C. for 30 min. A further aliquot of ethylene diamine (0.4 ml) is then added, and the mixture is heated at 160° C. for 50 min and finally at 150° C. for 2 h. The mixture is cooled to room temperature, and the volatiles are removed under reduced pressure. The residue is dissolved in dry methanol (4 ml), and the solution is cooled to 0° C. Sodium borohydride (15 mg, 0.4 mmol) is added, and the mixture is stirred for 18 h as it warms to room temperature. The mixture is quenched by the addition of water (30 ml) and extracted with dichloromethane (3×20 ml). The organic phases are combined, washed with saturated brine (50 ml), dried (MgSO4), filtered and evaporated under reduced pressure. The residue is purified by preparative reversed phase chromatography using 90% water/-acetonitrile to 100% acetonitrile as eluant. The pure product-containing fractions are combined and evaporated to dryness, and the residue is triturated with n-hexane containing a small amount of dichloromethane. The resulting colourless powder is recovered by filtration and dried.

1. temperaturethe mixture is heated at 140° C. for 30 min
2. temperaturethe mixture is heated at 160° C. for 50 min and finally at 150° C. for 2 h
3. temperatureThe mixture is cooled to room temperature
4. customthe volatiles are removed under reduced pressure
5. dissolutionThe residue is dissolved in dry methanol (4 ml)
6. temperaturethe solution is cooled to 0° C
7. customwarms to room temperature
8. customThe mixture is quenched by the addition of water (30 ml)
9. extractionextracted with dichloromethane (3×20 ml)
10. washwashed with saturated brine (50 ml)
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. customevaporated under reduced pressure
14. customThe residue is purified by preparative reversed phase chromatography
15. additionThe pure product-containing fractions
16. customevaporated to dryness
17. customthe residue is triturated with n-hexane containing a small amount of dichloromethane
18. filtrationThe resulting colourless powder is recovered by filtration
19. customdried

ORD record

ord-1fc69d82802c4427a570bf63a3a628ad

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07732435B2