3-(Benzyloxy)-5-bromopyridin-2-amine → Methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate

HRID 1426163

Reaktionsgleichung

Reaktionsgleichung von HRID 1426163
[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:27]([N:28]=[C:29]=[S:30])=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:29]2[S:30][C:18]3[C:27]([N:28]=2)=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[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

4

Edukt 2

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amineHCID 86639699HCID 86639699, Verbindung

Produkt 1

HCID 59225690Methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylateAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-(Benzyloxy)-5-bromopyridin-2-amine (1.50 g, 5.37 mmol) was added to a mixture of methyl 6-chloro-5-isothiocyanatonicotinate (1.23 g, 5.37 mmol) in DMF (4 mL). The reaction mixture was stirred at 80° C. for an hour, then at 110° C. for 2 hours. The reaction mixture was cooled, partitioned between dichloromethane (200 mL) and water (200 mL) and 2N NaOH (15 mL). The organic layer was washed with water and brine, dried, and concentrated. The residue was dissolved in warm dichloromethane (70 mL), and to this was added warm hexanes (40° C.) (250 mL). The solution was cooled to ambient temperature and the resulting solids were collected by filtration to afford methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate (1.77 g, 69.9% yield) as a white powder. 1H NMR (CDCl3) δ 3.98 (s, 3H), 5.15 (s, 2H), 7.35 (s, 1H), 7.46 (m, 5H), 8.10 (s, 1H), 8.42 (s, 1H), 8.76 (bs, 1H), 9.02 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between dichloromethane (200 mL) and water (200 mL) and 2N NaOH (15 mL)
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in warm dichloromethane (70 mL)
  7. additionto this was added
  8. temperaturewarm hexanes (40° C.) (250 mL)
  9. temperatureThe solution was cooled to ambient temperature
  10. filtrationthe resulting solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-85f317336324411c9ac02459e4189941
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

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