Boron tribromide → HCID 58777582, Verbindung

HRID 1371727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371727
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16]C)=[C:14]([O:18]C)[CH:13]=[C:12]([F:20])[C:11]=2[F:21])=[O:9])=[CH:6][N:5]=[C:4]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([OH:16])=[C:14]([OH:18])[CH:13]=[C:12]([F:20])[C:11]=2[F:21])=[O:9])=[CH:6][N:5]=[C:4]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:27][CH2:28]2)[N:3]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 58777551HCID 58777551, Verbindung

Produkt 1

HCID 58777582HCID 58777582, VerbindungAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-5,6-dimethoxy-phenyl)-methanone (100 mg, 0.212 mmol, Example 261) in methylene chloride (50 mL) cooled to −78° C. was added boron tribromide (2.19 mL, 2.190 mmol, 1 M solution in methylene chloride, Aldrich). The reaction mixture was warmed slowly to 0° C. over a period of 1 hour. After being stirred at 0° C. for 1 hour, the reaction was quenched with a solution of aqueous sodium bicarbonate. The aqueous layer was extracted with methylene chloride. The combined layers were washed with water and dried over anhydrous sodium sulfate. The solids were filtered off and the filtrate was concentrated in vacuo. Purification of the crude residue by reversed phase HPLC (C18, eluting with water and acetonitrile) yielded [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-5,6-dihydroxy-phenyl)-methanone as yellow solids (50 mg, 52%). HR-MS (ES, m/z) calculated for C17H20N5O5SF2 [(M+H)+] 444.1151, observed 444.1148.

Aufarbeitung

  1. customthe reaction was quenched with a solution of aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washThe combined layers were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification of the crude residue
  8. washby reversed phase HPLC (C18, eluting with water and acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-20fd62284a3d44c2a046f8c90853c1c9
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157455B2

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