Methanol → HCID 178429965, compound

HRID 1792803Notes

Reaction equation

HRID 1792803 reaction equation
C[O-].[Na+].CO.Cl.[NH2:7][C:8]([NH2:10])=[NH:9].Cl[C:12]([C:14]1[C:18]([CH3:19])=[CH:17][N:16]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][CH:21]=2)[CH:15]=1)=[O:13]>COCCOC.C(Cl)(Cl)Cl>[NH:9]([C:12]([C:14]1[C:18]([CH3:19])=[CH:17][N:16]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][CH:21]=2)[CH:15]=1)=[O:13])[C:8]([NH2:10])=[NH:7]

Participants

7

Reactant 4

HCID 887MethanolHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 220249394-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carbonyl chloride

Product 1

HCID 178429965HCID 178429965, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

1.4 g (25.5 mmol) of sodium methoxide is added at a temperature in the region of 20° C. under an argon atmosphere to 25 mL of methanol. After complete dissolution, 2.5 g (26.2 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 1 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 1.07 g (3.97 mmol) of 3-chlorocarbonyl-4-methyl-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 filtrate is partially concentrated to a volume of 5 to 10 mL and is then purified by silica gel chromatography [eluent: chloroform/methanol (75/25 by volume)]. After concentrating the fractions under reduced pressure and triturating in ethyl ether, 0.64 g of 3-guanidinocarbonyl-4-methyl-1-(quinol-4-yl)-1H-pyrrole is obtained in the form of an off-white solid melting at 215° C. Mass spectrum (EI): m/e 293 (M+.), m/e 234.

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. concentrationThe filtrate is partially concentrated to a volume of 5 to 10 mL
  16. customis then purified by silica gel chromatography [eluent: chloroform/methanol (75/25 by volume)]
  17. concentrationAfter concentrating the fractions under reduced pressure
  18. customtriturating in ethyl ether

Sources & evidence

ORD record
ord-1b5c08f7787d4c9ba741d3bb98e20248
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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