2-Chloro-3-isothiocyanatopyridine → N-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 1426156

Reaktionsgleichung

Reaktionsgleichung von HRID 1426156
[CH2:1]([O:8][C:9]1[C:10]([NH2:16])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:18]1[C:23]([N:24]=[C:25]=[S:26])=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C=O)C.O.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:25]2[S:26][C:18]3[C:23]([N:24]=2)=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 128680882-Chloro-3-isothiocyanatopyridineHCID 206265543-(Benzyloxy)-5-bromopyridin-2-amine

Produkt 1

HCID 16661301N-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-(Benzyloxy)-5-bromopyridin-2-amine (10.0 g, 35.83 mmol) was added to a mixture of 2-chloro-3-isothiocyanatopyridine (6.112 g, 35.83 mmol) in DMF. The reaction was stirred at 80° C. for an hour, then at 110° C. for two hours. The reaction was cooled, diluted in water (200 mL) and 2N NaOH (35 mL), stirred for 30 minutes, and then filtered. The wet solids were washed with water, then dissolved in dichloromethane (300 mL) dried over MgSO4, and filtered. Hexane (300 mL) was added to the combined filtrates, the mixture was concentrated to 500 mL, and then mixture stirred for 30 minutes. The mixture was filtered to afford the first crop of the title compound. The mother liquor was concentrated to 500 mL (until most of the dichloromethane was removed), filtered, washed with hexanes to afford a second crop of the title compound. The two crops combined afforded the title compound (10.2 g, 68.7%) as light yellow crystals: 1H NMR (CDCl3) δ 5.14 (s, 2H), 7.30-7.33 (m, 2H), 7.42-7.48 (m, 5H), 7.87 (d, 1H), 8.10 (s, 1H), 8.40 (d, 1H), 8.67 (bs, 1H).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washThe wet solids were washed with water
  4. dissolutiondissolved in dichloromethane (300 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. additionHexane (300 mL) was added to the combined filtrates
  8. concentrationthe mixture was concentrated to 500 mL
  9. stirringmixture stirred for 30 minutes
  10. filtrationThe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-5c51f99cc0ce4650b01b9a24e3ef327b
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

Verknüpfte Notizen

Wird geladen…