Hydrochloric Acid → HCID 178429412, compound

HRID 1792810Notes

Reaction equation

HRID 1792810 reaction equation
C[O-].[Na+].[ClH:4].[NH2:5][C:6]([NH2:8])=[NH:7].[Cl:9][C:10]([C:12]1[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:13]=1)=[O:11].Cl>COCCOC.C(Cl)(Cl)Cl.C(O)C.O1CCOCC1.CO>[ClH:9].[ClH:4].[NH:7]([C:10]([C:12]1[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:13]=1)=[O:11])[C:6]([NH2:8])=[NH:5]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 220249704,5-Dimethyl-1-(quinolin-4-yl)-1H-pyrrole-3-carbonyl chloride

Product 1

HCID 178429412HCID 178429412, compoundYield 61.6%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

1.78 g (33 mmol) of sodium methoxide are added at a temperature in the region of 20° C. under an argon atmosphere to 20 mL of methanol. After complete dissolution, 3.34 g (35 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 25 mL of 1,2-dimethoxyethane and then again concentrated to dryness. The residue is suspended in a mixture of 75 mL of tetrahydrofuran and 50 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere and then 1.17 g (4.1 mmol) of 3-chlorocarbonyl-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole, dissolved in 25 mL of chloroform, are added thereto. After stirring at a temperature in the region of 20° C. for 18 hours, 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 filtering, a gum is obtained, which gum is triturated in 50 mL of methanol and filtered. The solution obtained is partially concentrated to a volume of 5 to 10 mL and then purified by silica gel chromatography [eluent: chloroform/methanol (90/10 and then 70/30 by volume)]. After concentrating the fractions under reduced pressure, an oil is obtained, which oil is dissolved in ethanol and to which is added 4 mL of a 5.3N solution of hydrochloric acid in dioxane. The solution obtained is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is triturated in a mixture of isopropanol and isopropyl acetate. 0.96 g of 3-guanidinocarbonyl-4,5-dimethyl-1-(quinol-4-yl)-1H-pyrrole dihydrochloride is thus obtained in the form of a yellow solid which decomposes at a temperature of greater than 260° C. Mass spectrum (EI): m/e 307 (M+) m/e 248. IR spectrum (KBr): 3371, 3103, 2622, 1694, 1599, 1495, 1423, 1308, 1251, 1194, 1093 and 754 cm−1.

Workup

  1. additionare added
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. concentrationagain concentrated to dryness
  5. additionThe residue is suspended in a mixture of 75 mL of tetrahydrofuran and 50 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere
  6. additionare added
  7. stirringAfter stirring at a temperature in the region of 20° C. for 18 hours
  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 filtering
  12. customa gum is obtained
  13. customwhich gum is triturated in 50 mL of methanol
  14. filtrationfiltered
  15. customThe solution obtained
  16. concentrationis partially concentrated to a volume of 5 to 10 mL
  17. custompurified by silica gel chromatography [eluent
  18. concentrationAfter concentrating the fractions under reduced pressure
  19. customan oil is obtained
  20. customThe solution obtained
  21. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  22. customto give a residue which
  23. customis triturated in a mixture of isopropanol and isopropyl acetate

Sources & evidence

ORD record
ord-d0bdaf28d9484854bfe56b4706d69540
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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