Isoquinoline-1-carboxylic acid → HCID 178481697, Verbindung

HRID 33221

Reaktionsgleichung

Reaktionsgleichung von HRID 33221
OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:23][NH:24][C:25](=[S:28])[NH:26][NH2:27].[C:29]1([C:39](O)=O)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][N:30]=1>CN(C)C=O.C(N(CC)CC)C>[C:29]1([C:39]2[N:24]([CH3:23])[C:25]([SH:28])=[N:26][N:27]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][N:30]=1

Komponenten

7

Edukt 4

HCID 68092Isoquinoline-1-carboxylic acidHCID 2723853N-MethylhydrazinecarbothioamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 178481697HCID 178481697, VerbindungAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Hydroxybenzotriazole (0.078 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) and triethylamine were added successively to a cooled solution (0° C.) of 4-methyl-3-thiosemicarbazide (0.061 g) and 1-isoquinoline carboxylic acid (0.10 g) in dimethylformamide (3 ml). Following addition the cooling bath was removed and the mixture was stirred at room temperature over night and then the reaction mixture was evaporated to dryness. To the residue was added sodium hydroxide solution (0.5 M, 5 ml) and the mixture was stirred at 80° C. for 3 h. The mixture was cooled to room temperature and the pH adjusted to pH 6 using hydrochloric acid solution (2M) and the resulting precipitate was filtered and dried in vacuo to give the title compound (0.11 g, 78%) as an off-white solid.

Aufarbeitung

  1. additionaddition the cooling bath
  2. customwas removed
  3. customthe reaction mixture was evaporated to dryness
  4. additionTo the residue was added sodium hydroxide solution (0.5 M, 5 ml)
  5. stirringthe mixture was stirred at 80° C. for 3 h
  6. temperatureThe mixture was cooled to room temperature
  7. filtrationthe resulting precipitate was filtered
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bf1242f4a62f4ab2a9d086f066f1c384
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429579B2

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