Methanol → HCID 178429410, compound

HRID 1792789Notes

Reaction equation

HRID 1792789 reaction equation
[Na].CO.Cl.[NH2:5][C:6]([NH2:8])=[NH:7].Cl.[Cl:10][C:11]([C:13]1[CH:17]=[CH:16][N:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[C:14]=1[CH3:28])=[O:12]>COCCOC>[ClH:10].[NH:7]([C:11]([C:13]1[CH:17]=[CH:16][N:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[C:14]=1[CH3:28])=[O:12])[C:6]([NH2:8])=[NH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 22024981HCID 22024981, compound

Product 1

HCID 178429410HCID 178429410, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

0.795 g (33.1 mmol) of sodium is added at 20° C. under an argon atmosphere to 30 mL of methanol. After complete dissolution, 2.97 g (31.2 mmol) of guanidine hydrochloride are added. After stirring at 20° C. for 0.5 hour, the reaction mixture is filtered under an argon atmosphere. The filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue that is dissolved in 15 mL of 1,2-dimethoxyethane. 2 g of 3-chlorocarbonyl-2-methyl-1-(quinol-2-yl)-1H-pyrrole hydrochloride, suspended in 15 mL of 1,2-dimethoxyethane, are then added at 20° C. under an argon atmosphere. After stirring at 20° C. for 8 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue that is triturated in 100 mL of water for 16 hours. After filtering off and drying the solid residue under reduced pressure (2.7 kPa), a residue is obtained, which residue is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (86/7/7 by volume) and then dichloromethane/methanol/20% aqueous ammonia (96/24/2 by volume)]. After concentrating the fractions under reduced pressure, a beige-coloured solid is obtained, which solid is triturated in 100 mL of N hydrochloric acid for 15 hours. After filtration, the solid residue is recrystallised under hot conditions from 30 mL of methanol to give 0.82 g of 3-guanidinocarbonyl-2-methyl-1-(quinol-2-yl)-1H-pyrrole hydrochloride in the form of a pinkish solid melting at 250° C. Mass spectrum (EI): m/e 293 (M+.), m/e 206 (base peak).

Workup

  1. additionare added
  2. filtrationthe reaction mixture is filtered under an argon atmosphere
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  4. customto give a residue that
  5. additionare then added at 20° C. under an argon atmosphere
  6. stirringAfter stirring at 20° C. for 8 hours
  7. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  8. customto give a residue that
  9. customis triturated in 100 mL of water for 16 hours
  10. filtrationAfter filtering off
  11. customdrying the solid residue under reduced pressure (2.7 kPa)
  12. customa residue is obtained
  13. customwhich residue is purified by flash chromatography [eluent
  14. concentrationAfter concentrating the fractions under reduced pressure
  15. customa beige-coloured solid is obtained
  16. customwhich solid is triturated in 100 mL of N hydrochloric acid for 15 hours
  17. filtrationAfter filtration
  18. customthe solid residue is recrystallised under hot conditions from 30 mL of methanol

Sources & evidence

ORD record
ord-ac28c993563b4f95b88d0b1c4390b3b0
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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