Sodium hydride → 2-(4-Chloro-3-cyclopropyl-5-phenyl-pyrazolo[3,4-c]pyridazin-1-yl)-1-pyrrolidin-1-yl-ethanone

HRID 588590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588590
[H-].[Na+].[Cl:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]=[C:6]2[NH:16][N:17]=[C:18]([CH:19]3[CH2:21][CH2:20]3)[C:5]=12.Cl[CH2:23][C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]=[C:6]2[N:16]([CH2:23][C:24]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:25])[N:17]=[C:18]([CH:19]3[CH2:21][CH2:20]3)[C:5]=12

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 884401-(Chloroacetyl)pyrrolidineHCID 86717280HCID 86717280, Verbindung

Produkt 1

HCID 867172902-(4-Chloro-3-cyclopropyl-5-phenyl-pyrazolo[3,4-c]pyridazin-1-yl)-1-pyrrolidin-1-yl-ethanoneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in mineral oil, 18 mg, 0.44 mmol) was added to a solution of 4-chloro-3-cyclopropyl-5-phenyl-1H-pyrazolo[3,4-c]pyridazine (100 mg, 0.37 mmol) and 2-chloro-1-(pyrrolidin-1-yl)ethanone (82 mg, 0.55 mmol) in dry DMF (3 mL) at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, CH2Cl2/diethyl ether 8:2) to provide Compound Iee as a solid (65 mg).

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, CH2Cl2/diethyl ether 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-5b90b7c0b19f4b43a87066a381f77a24
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227976B2

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