Pyrazole → HCID 178486388, Verbindung

HRID 1056921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056921
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:15]3[CH:16]=[C:17]4[O:25][CH2:24][O:23][C:18]4=[CH:19][C:20]=3[C:21](=[O:22])[C:13]=2[C:12]2[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:26][CH3:27])[CH:11]=2)[C:6]1=[O:30].[H-].[Na+].[NH:33]1[CH:37]=[CH:36][CH:35]=[N:34]1>CN(C=O)C.O>[NH:33]1[CH:37]=[CH:36][C:35]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:15]4[CH:16]=[C:17]5[O:25][CH2:24][O:23][C:18]5=[CH:19][C:20]=4[C:21](=[O:22])[C:13]=3[C:12]3[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:26][CH3:27])[CH:11]=3)[C:6]2=[O:30])=[N:34]1

Komponenten

6

Edukt 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 106242586-(3-bromo-1-propyl)-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline

Produkt 1

HCID 178486388HCID 178486388, VerbindungAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-(3-Bromo-1-propyl)-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (5y) (0.2113 g, 0.448 mmol) was added to sodium hydride (86.8 mg of a 60% suspension in mineral oil, 2.17 mmol) and pyrazole (0.1749 g, 2.57 mmol) in DMF (50 mL) and the reaction mixture was heated at 60° C. for 4 h. The reaction mixture was diluted with water (200 mL) and extracted with chloroform (200 mL). The organic layer was washed with water (7×200 mL) and concentrated. Benzene was added (2×30 mL) and the mixture was concentrated again. The residue was dissolved in chloroform (4 mL) and diethyl ether (50 mL) was added. The precipitate was washed with diethyl ether (100 mL) and a dark red solid (118.5 mg, 57.6%) was obtained: mp 262-264° C. (dec). IR (film) 3462, 3104, 2918, 1693, 1640, 1557, 1495, 1488, 1430, 1394, 1308, 1284, 1251, 1205, 868, 785, 769 cm−1; 1H NMR (DMSO-d6) δ 7.97 (s, 1H), 7.65 (d, J=1.5 Hz, 1H), 7.61 (s, 1H), 6.57 (s, 1H), 6.97 (s, 1H), 6.68 (s, 1H), 6.33 (s, 1H), 6.05 (s, 2H), 4.40 (m, 4H), 4.01 (s, 3H), 3.96 (s, 3H), 2.45 (m, 2H); ESIMS m/z (rel intensity) 460 (MH+, 100). Anal. (C25H21N3O6.0.75H2O) C, H, N.

Aufarbeitung

  1. extractionextracted with chloroform (200 mL)
  2. washThe organic layer was washed with water (7×200 mL)
  3. concentrationconcentrated
  4. additionBenzene was added (2×30 mL)
  5. concentrationthe mixture was concentrated again
  6. dissolutionThe residue was dissolved in chloroform (4 mL)
  7. additiondiethyl ether (50 mL) was added
  8. washThe precipitate was washed with diethyl ether (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-c9ce69f1191f428fbba7f75f3ead2dd6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399660B2

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