反应详情

80 Milliliters of 20% hydrous pyridine was added to 5.76 g of 4-methylaminomethyliminomethylaminobenzoic acid.hydrochloride, 6.0 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 5.3 g of DCC and 217 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 5 days at room temperature. Then, the precipitate was collected by filtration and washed with 120 ml of warm DMF. To this collected precipitate was added 300 ml of water, followed by stirring for 24 hours at room temperature, and the precipitate was filtered. Each of the reaction filtrate, warm DMF wash liquid and aqueous filtrate obtained above was concentrated under reduced pressure. The resulting residues were combined and 70 ml of DMF was added thereto. The solution was added dropwise to 700 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain a crude product. Then, the product was subjected to silica gel column chromatography using methyl ethyl ketone-water-acetic acid (80:15:5) as an eluent, and the desired fractions were collected and the solvent was distilled off under reduced pressure. To the residue were added 50 ml of methanol and 3.3 ml of concentrated hydrochloric acid, and the solution was added dropwise to a mixed liquid of 500 ml of acetone and 200 ml of ether, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 5.78 g of the desired product.

1. temperatureunder cooling with ice
2. custom5 days
3. customat room temperature
4. filtrationThen, the precipitate was collected by filtration
5. washwashed with 120 ml of warm DMF
6. additionTo this collected precipitate was added 300 ml of water
7. stirringby stirring for 24 hours at room temperature
8. filtrationthe precipitate was filtered
9. temperatureEach of the reaction filtrate, warm DMF
10. washwash liquid and aqueous filtrate
11. customobtained
12. concentrationabove was concentrated under reduced pressure
13. addition70 ml of DMF was added
14. additionThe solution was added dropwise to 700 ml of acetone
15. stirringby stirring for 24 hours
16. temperatureunder cooling with ice
17. filtrationThen, the precipitate was collected by filtration
18. customto obtain a crude product
19. customthe desired fractions were collected
20. distillationthe solvent was distilled off under reduced pressure
21. additionTo the residue were added 50 ml of methanol and 3.3 ml of concentrated hydrochloric acid
22. additionthe solution was added dropwise to a mixed liquid of 500 ml of acetone and 200 ml of ether
23. stirringby stirring for 24 hours
24. temperatureunder cooling with ice
25. filtrationThen, the precipitate was collected by filtration