Diisopropylethylamine → HCID 178478954, compound

Temperature

80 °C

A 678 mg portion of [(1-trityl-1H-imidazol-4-yl)methyl]amine was dissolved in 10.0 ml of acetonitrile, and 0.52 ml of diisopropylethylamine and 316 mg of the 6-chloro-N-(4-fluorophenyl)-N′-phenyl-1,3,5-triazine-2,4-diamine synthesized in Reference Example 1 were added thereto and stirred at 80° C. for 3 days. After cooling down to room temperature, the reaction solution was mixed with water and extracted with ethyl acetate. The organic layer was washed with citric acid aqueous solution and saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (99:1) to obtain a crude product. This crude product was dissolved in 9 ml of acetic acid and 1 ml of water and stirred at 70° C. for 2 hours. After evaporation of the reaction solution under a reduced pressure, the residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (90:10) to obtain a crude product. This crued product was dissolved in ethyl acetate and mixed with 4 M hydrochloric acid ethyl acetate solution, and the thus formed crystals were collected by filtration and dried to obtain 306 mg of N-(4-fluorophenyl)-N′-(1H-imidazol-4-ylmethyl)-N″-phenyl-1,3,5-triazine-2,4,6-triamine hydrochloride as colorless crystals.

1. additionwere added
2. temperatureAfter cooling down to room temperature
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with citric acid aqueous solution and saturated brine
5. customdried
6. customThe solvent was evaporated under a reduced pressure
7. washeluted with chloroform:methanol (99:1)
8. customto obtain a crude product
9. customAfter evaporation of the reaction solution under a reduced pressure
10. additionthe residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order
11. extractionextracted with ethyl acetate
12. washThe organic layer was washed with saturated brine
13. customdried
14. customThe solvent was evaporated under a reduced pressure
15. washeluted with chloroform:methanol (90:10)
16. customto obtain a crude product
17. filtrationthe thus formed crystals were collected by filtration
18. customdried

ORD record

ord-0e884dc45de24d5aaf23fb4316ebc00b

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375222B2