Guanidine Hydrochloride → HCID 178513070, compound

HRID 492196Notes

Reaction equation

HRID 492196 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].Cl.Cl[C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:14]=1)=[O:12].C(OCC)(=O)C.CO>CO.O1CCCC1.ClCCl.ClCCl>[NH:4]([C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:14]=1)=[O:12])[C:3]([NH2:5])=[NH:2]

Participants

8

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 21584119Ethylacetate methanolHCID 86596413HCID 86596413, compound

Product 1

HCID 178513070HCID 178513070, compoundYield 59.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

1.25 g (13.09 mmol) of guanidine hydrochloride are added to a solution of 0.71 mg (13.14 mmol) of sodium methoxide in 10 cm3 of methanol at a temperature in the region of 22° C. under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 2 hours, the solvent is evaporated off under reduced pressure (2.7 kPa). The residue, placed under an argon atmosphere, is taken up in 20 cm3 of a tetrahydrofuran/dichloromethane (1/1 by volume) mixture and then 0.9 g (2.62 mmol) of 3-chlorocarbonyl-1-(quinol-8-yl)-1H-indole hydrochloride, dissolved in 5 cm3 of the same tetrahydrofuran/dichloromethane mixture, is added thereto. After 15 hours at a temperature in the region of 22° C. and then heating at a temperature in the region of 60° C. with stirring for 1.5 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in dichloromethane. The insoluble material is then filtered off and discarded, and the filtrate is concentrated under reduced pressure (2.7 kPa). The residue obtained is taken up in an ethyl acetate/methanol (8/2 by volume) mixture and the resulting precipitate is filtered off. A white solid is obtained, which solid is crystallised under hot conditions from 10 cm3 of ethanol. The crystals formed are filtered off and dried under vacuum (2.7 kPa) to give 0.51 g of 3-guanidinocarbonyl-1-(quinol-8-yl)-1H-indole in the form of white crystals melting at 172° C. Mass spectrum (EI): m/e 329 (M+·), m/e 271.

Workup

  1. customthe solvent is evaporated off under reduced pressure (2.7 kPa)
  2. additionis added
  3. waitAfter 15 hours at a temperature in the region of 22° C.
  4. temperatureheating at a temperature in the region of 60° C.
  5. stirringwith stirring for 1.5 hours
  6. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customto give a residue which
  8. filtrationThe insoluble material is then filtered off
  9. concentrationthe filtrate is concentrated under reduced pressure (2.7 kPa)
  10. customThe residue obtained
  11. filtrationthe resulting precipitate is filtered off
  12. customA white solid is obtained
  13. customwhich solid is crystallised under hot conditions from 10 cm3 of ethanol
  14. customThe crystals formed
  15. filtrationare filtered off
  16. customdried under vacuum (2.7 kPa)

Sources & evidence

ORD record
ord-beb72b2899384b9992b917f4535d7310
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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