Dimethylmethylenammonium chloride → 2-Dimethylaminomethyl-9-hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one hydrochloride

HRID 2069109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069109
[OH:1][C:2]1[C:3]2[C:4]3[N:15]=[CH:14][S:13][C:5]=3[NH:6][C:7](=[O:12])[C:8]=2[CH:9]=[CH:10][CH:11]=1.[Cl-:16].[CH3:17][N+:18]([CH3:20])=[CH2:19]>CN(C=O)C.C(#N)C>[ClH:16].[CH3:17][N:18]([CH2:20][C:14]1[S:13][C:5]2[NH:6][C:7](=[O:12])[C:8]3[CH:9]=[CH:10][CH:11]=[C:2]([OH:1])[C:3]=3[C:4]=2[N:15]=1)[CH3:19]

Komponenten

4

Edukt 2

HCID 11051579Dimethylmethylenammonium chlorideHCID 580160609-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

Produkt 1

HCID 670764312-Dimethylaminomethyl-9-hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one hydrochlorideAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 9-hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one in DMF/acetonitrile (3 ml, 1:2) was added dimethyl-methylene-ammonium chloride (0.043 g, 0.46 mmol) and the resulting mixture was refluxed under Ar for 42 hours. After cooling and concentration, the residue was purified via flash chromatography on SiO2 to give the title compound (0.008 g, a 13% yield) as solid. m.p.>250° C.; 1H NMR (400 MHz, DMSO) δ 2.36 (s, 6H, N(CH3)2), 3.93 (m, 2H, CH2N), 7.24 (d, 1H, Ar), 7.44 (t, 1H, Ar), 7.74 (d, 1H, Ar), 10.23 (s, 1H, OH), 12.30 (s, 1H, NH); 13C NMR (100.6 MHz, DMSO) δ 46.83, 61.38, 119.94, 120.56, 121.00, 126.83, 129.95, 131.75, 137.39, 154.41, 162.54.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed under Ar for 42 hours
  2. temperatureAfter cooling
  3. concentrationconcentration
  4. customthe residue was purified via flash chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-eaa35daa1e174d15bdb3ea0b7e1b7dec
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299090B2

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