5-Isocyanato-1,2,3-trimethoxybenzene → 1-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]3-(3,4,5-trimethoxy-phenyl)-urea

HRID 1838453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838453
[NH2:1][CH:2]1[CH2:6][CH:5]([N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:17])[C:11]=3[C:10]3=[N:18][O:19][C:20]([CH3:21])=[C:9]3[C:8]2=[O:22])[CH:4]=[CH:3]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:35]=[C:36]=[O:37])[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:17][C:12]1[C:11]2[C:10]3[C:9](=[C:20]([CH3:21])[O:19][N:18]=3)[C:8](=[O:22])[N:7]([CH:5]3[CH2:6][CH:2]([NH:1][C:36]([NH:35][C:27]4[CH:26]=[C:25]([O:24][CH3:23])[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=4)=[O:37])[CH:3]=[CH:4]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 5177665-Isocyanato-1,2,3-trimethoxybenzeneHCID 12094964HCID 12094964, Verbindung

Produkt 1

HCID 103018101-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]3-(3,4,5-trimethoxy-phenyl)-ureaAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 5-(4amino-cyclopent-2-enyl)9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (69 mg, 0.22 mmol) in CH2Cl2 (5 mL) was added 3,4,5-trimethoxy-isocyanato benzene (55 mg, 0.26 mmol) and DMAP (catalytic amount) and stirred at rt. for 18 hours. The mixture was diluted with CH2Cl2, washed (brine), dried Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the title compound (116 mg, 100%). Mass Spectrum (FIA) (m/z) 425.3 (M+1) 1H NMR (CDCl3): δ 7.45 (d, 1H); 7.40 (t, 1H); 7.33 (d, 1H); 6.58 (m, 3H); 5.95 (m, 1H); 5.83 (m, 1H); 5.18 (s, 1H); 3.78 (s, 9H); 2.98 (m, 2H); 2.05 (m, 2H).

Aufarbeitung

  1. washwashed (brine), dried Na2SO4),
  2. filtrationfiltered
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-df7a22b50b754620a58738e72c881738
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673809B2

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