Sodium Hydroxide → 7-Chloro-2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazine

HRID 1582322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582322
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[N:16]([CH2:17][C@H:18]2[CH2:20][C@@H:19]2[CH3:21])[C:10]2[C:11](=O)[NH:12][N:13]=[CH:14][C:9]=2[C:8]=1[CH3:22].[OH-].[Na+]>>[Cl:3][C:11]1[N:12]=[N:13][CH:14]=[C:9]2[C:8]([CH3:22])=[C:7]([CH3:6])[N:16]([CH2:17][C@H:18]3[CH2:20][C@@H:19]3[CH3:21])[C:10]=12

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 121104562,3-Dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazin-7-one

Produkt 1

HCID 121104577-Chloro-2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrolo[2,3-d]pyridazineAusbeute 92 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Phosphorus oxychloride (55 ml, 590 mmol) was added to 2,3-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]-6,7-dihydropyrrolo[2,3-d]pyridazine-7-one (6.95 g, 30.1 mmol) and the mixture was stirred at 90° C. for 3.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into ice-water. The aqueous solution was neutralized with a 5N aqueous sodium hydroxide solution and extracted with methylene chloride. The extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated in vacuo. Hexane was added to the residue and the precipitate was collected by filtration to afford the desired compound (6.90 g, 92.0%) as a pale yellow powder.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionHexane was added to the residue
  7. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2b05e176d88e4146b9f4173cd7e9cf57
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734181B2

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