Methanesulfonic Acid → 6-amidino-1-carboxymethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoate

HRID 1419248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419248
CS(O)(=O)=O.[NH:6]1[CH2:10][CH2:9][N:8]=[C:7]1[NH:11][C:12]1[CH:38]=[CH:37][C:15]([C:16]([O:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29](=[NH:31])[NH2:30])[CH:25]=3)[C:20]=2[CH2:32][C:33]([O:35]C)=[O:34])=[O:17])=[CH:14][CH:13]=1>>[NH:8]1[CH2:9][CH2:10][N:6]=[C:7]1[NH:11][C:12]1[CH:38]=[CH:37][C:15]([C:16]([O:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29](=[NH:30])[NH2:31])[CH:25]=3)[C:20]=2[CH2:32][C:33]([OH:35])=[O:34])=[O:17])=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 6395Methanesulfonic AcidHCID 867539746-amidino-1-methoxycarbonylmethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoate

Produkt 1

HCID 867539756-amidino-1-carboxymethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoateAusbeute 48,8 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

45 Milliliters of 10% aqueous methanesulfonic acid solution was added to 500 mg of 6-amidino-1-methoxycarbonylmethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoate.dimethanesulfonate, followed by stirring for 5 hours at 80° C. After leaving the mixture for cooling, 350 mg of active carbon was added to the reaction mixture, followed by stirring for 30 minutes at room temperature. Insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. To the residue was added a small amount of water. The solution was added dropwise to a mixed liquid of 150 ml of acetone and 50 ml of ether, followed by stirring for 1 hour under cooling with ice. Then, the precipitate was collected by filtration and washed with a small amount of acetone to obtain 236.1 mg of the desired product.

Aufarbeitung

  1. customAfter leaving the mixture
  2. temperaturefor cooling
  3. addition350 mg of active carbon was added to the reaction mixture
  4. stirringby stirring for 30 minutes at room temperature
  5. filtrationInsoluble matter was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionTo the residue was added a small amount of water
  8. additionThe solution was added dropwise to a mixed liquid of 150 ml of acetone and 50 ml of ether
  9. stirringby stirring for 1 hour
  10. temperatureunder cooling with ice
  11. filtrationThen, the precipitate was collected by filtration
  12. washwashed with a small amount of acetone

Quellen und Nachweise

ORD-Eintrag
ord-a853fd221396422ea8a889b6c46edb0e
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05885990

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