Pyridine → HCID 86652271, Verbindung

HRID 1256294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256294
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.N1C=CC=CC=1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=2)[CH:3]=1

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amine

Produkt 1

HCID 86652271HCID 86652271, VerbindungAusbeute 51,3 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 20 mL scintillation vial was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1.1, 0.207 g, 1.131 mmol) and pyridine (2.84 ml, 35.1 mmol) and the solution was cooled to 0° C. To the yellow solution was added 4-(trifluoromethoxy)benzoyl chloride (0.508 g, 2.262 mmol) to give an orange suspension. The reaction mixture was stirred for one hour, quenched by the addition of saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure in the presence of silica gel. The silica-adsorbed material was then purified by silica gel chromatography (25-75% ethyl acetate/hexanes gradient) to afford the desired compound N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide 14A as an orange solid (215 mg, 51% yield); ESI-MS: m/z 370.0 (M+H)+.

Aufarbeitung

  1. customto give an orange suspension
  2. customquenched by the addition of saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure in the presence of silica gel
  7. customThe silica-adsorbed material was then purified by silica gel chromatography (25-75% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-05b2e17cd2974551b7be0fe01a73a898
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461163B2

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