Methanesulfonyl chloride → HCID 68892450, Verbindung

HRID 1396546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396546
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH2:17])=[N:14][CH:15]=3)[N:10]([CH3:18])[N:9]=2)=[CH:4][C:3]=1[F:19].C(=O)=O.CC(C)=O.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.CCOC(C)=O>[NH2:17][C:13]1[N:12]=[C:11]2[N:10]([CH3:18])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:28]([CH3:27])(=[O:30])=[O:29])=[C:3]([F:19])[CH:4]=3)[C:16]2=[CH:15][N:14]=1

Komponenten

6

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 18522661Acetone cardiceHCID 68891998HCID 68891998, Verbindung

Produkt 1

HCID 68892450HCID 68892450, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

3-(4-Amino-3-fluoro-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Example 58) (0.13 g, 0.50 mmol) is dissolved in pyridine (1.5 ml) under an inert atmosphere of argon. The reaction mixture is cooled to −10° C. (dry ice/acetone bath) then methanesulfonyl chloride (0.078 ml, 0.75 mmol) is added drop wise over a period of 15 minutes. The reaction mixture is stirred at −10° C. for 30 minutes then allowed to warm to room temperature and stirred for further 3 hours. The reaction mixture is diluted with EtOAc (100 ml) and washed with water (3×40 ml) and brine (10 ml). The organic portion is dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with hot EtOAc (plus few drops of MeOH), filtered and dried under vacuum at 50° C. for 3 hours to afford the title compound as an off-white solid.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for further 3 hours
  3. washwashed with water (3×40 ml) and brine (10 ml)
  4. dry with materialThe organic portion is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid is triturated with hot EtOAc (plus few drops of MeOH)
  8. filtrationfiltered
  9. customdried under vacuum at 50° C. for 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-d9fe7c937a5840fc99d71897cfc782ad
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901134B2

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