5-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one → N-[4(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]2-oxo-2-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 1838452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838452
[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.[O:23]=[C:24]([C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)[C:25](Cl)=[O:26]>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:25](=[O:26])[C:24](=[O:23])[C:28]4[CH:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=4)[CH:3]=[CH:4]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 120949645-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-oneHCID 226400793,4,5-Trimethoxyphenyl-2-oxoacetyl chloride

Produkt 1

HCID 18753704N-[4(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]2-oxo-2-(3,4,5-trimethoxy-phenyl)-acetamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 5-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (50 mg, 0.216 mmol) in CH2Cl2 (2 mL) was added oxo-(3,4,5-trimethoxy-phenyl)acetyl chloride (80 mg, 0.33 mmol, prepared from its acid and oxalyl chloride) and DMAP (catalytic amount) and stirred at r.t. 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 (33 mg, 38%). Mass Spectrum (FIA) (m/z) 538A 4 (A+1). 1H NMR (CDCl3): δ 7.80 (d, 1H); 7.50 (t, 1H); 7.35 (d, 1H); 6.00 (m, 2H); 5.40 (m, 1H); 5.21 (m, 111); 3.80-3.90 (m, 1H); 2.95 (s, 3H); 2.30 (m, 1H).

Aufarbeitung

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f0f0ad6a9cd04a22aac3b19ca9340fa6
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673809B2

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