9-methoxy-4H-thieno[2,3-c]isoquinolin-5-one → 2-Dimethylaminomethyl-9-methoxythieno[2,3-c]isoquinolin-5(4H)-one hydrochloride

HRID 1524622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524622
[CH3:1][O:2][C:3]1[C:4]2[C:5]3[CH:16]=[CH:15][S:14][C:6]=3[NH:7][C:8](=[O:13])[C:9]=2[CH:10]=[CH:11][CH:12]=1.[Cl-:17].[CH3:18][N+:19](=[CH2:21])[CH3:20]>CN(C=O)C.CC#N>[ClH:17].[CH3:18][N:19]([CH2:21][C:15]1[S:14][C:6]2[NH:7][C:8](=[O:13])[C:9]3[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=3[C:5]=2[CH:16]=1)[CH3:20]

Komponenten

5

Edukt 2

HCID 99646519-methoxy-4H-thieno[2,3-c]isoquinolin-5-oneHCID 11051579Dimethylmethylenammonium chloride

Produkt 1

HCID 690042762-Dimethylaminomethyl-9-methoxythieno[2,3-c]isoquinolin-5(4H)-one hydrochlorideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

9-Methoxythieno[2,3-c]isoquinolin-5(4H)-one (Pellicciari, R., et al., Farmaco, 2003, 58, 851-858) (0.20 g, 0.86 mmol), was dissolved in a mixture of dry DMF (1 ml) and dry MeCN (2 ml) and treated with N,N-dimethyl(methylene)ammonium chloride (1.2 mmol) prepared according to a known procedure (Kinast, G. et al. Angew. Chem. Int. Ed. Engl. 1976, 15, 239-240. Bohme, H et al. Chem. Ber. 1960, 93, 1305). The reaction mixture was refluxed overnight. The formed solid was then filtered and washed with dry diethyl ether to give title compound (83% yield) as a solid. mp 264-265° C.

Aufarbeitung

  1. customprepared
  2. temperatureThe reaction mixture was refluxed overnight
  3. filtrationThe formed solid was then filtered
  4. washwashed with dry diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d9539b9192404bc6ac401d985707fba9
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079915B2

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