Guanidine Hydrochloride → HCID 178513074, Verbindung

Temperatur

20 °C

1.19 g (22 mmol) of sodium methoxide are added to 25 mL of methanol at a temperature in the region of 20° C. under an argon atmosphere. After total dissolution, 2.2 g (23 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 0.5 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue, which is suspended in 50 mL of 1,2-dimethoxyethane and then concentrated to dryness again. The residue is suspended in a mixture of 100 mL of tetrahydrofuran and 100 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere, and 1.12 g (3.78 mmol) of 3-chlorocarbonyl-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole dissolved in 25 mL of chloroform are then added. After stirring for 17 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue, which is triturated in 100 mL of water. After filtration, a gum is obtained, which is dissolved in 50 mL of methanol. The solution is partially concentrated to a volume of from 5 to 10 mL and then purified by chromatography on silica gel [eluent: chloroform/methanol (75/25 by volume)]. After the fractions containing the expected product have been concentrated to dryness under reduced pressure, the residue is dissolved in 20 mL of methanol, and 2 mL of 6 N hydrochloric dioxane are added. The solution obtained is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is then triturated in a mixture of dichloromethane and diethyl ether and filtered, giving 0.77 g of 4-cyclopropyl-3-guanidinocarbonyl-1-(quinolin-4-yl)-1H-pyrrole in the form of a yellow solid melting at 185° C. Mass spectrum (EI): m/e 319 (M+.) (base peak), m/e 260, m/e 231.

1. additionare added
2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
3. customto give a residue, which
4. concentrationconcentrated to dryness again
5. additionThe residue is suspended in a mixture of 100 mL of tetrahydrofuran and 100 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere
6. additionare then added
7. stirringAfter stirring for 17 hours at a temperature in the region of 20° C.
8. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
9. customto give a residue, which
10. customis triturated in 100 mL of water
11. filtrationAfter filtration
12. customa gum is obtained
13. concentrationThe solution is partially concentrated to a volume of from 5 to 10 mL
14. custompurified by chromatography on silica gel [eluent: chloroform/methanol (75/25 by volume)]
15. additionAfter the fractions containing the expected product
16. concentrationhave been concentrated to dryness under reduced pressure
17. dissolutionthe residue is dissolved in 20 mL of methanol
18. addition2 mL of 6 N hydrochloric dioxane are added
19. customThe solution obtained
20. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
21. customthe residue is then triturated in a mixture of dichloromethane and diethyl ether
22. filtrationfiltered

ORD-Eintrag

ord-488f452e1c6146b4a870ed73f4b787fe

Quelldatensatz

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07078414B2