Acetic Acid → Methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate

HRID 522697

Reaktionsgleichung

Reaktionsgleichung von HRID 522697
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:2]=1.[NH2:15][C:16]1[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=1.C(O)(=O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH:15][C:16]3[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=3)=[CH:9][CH:8]=2)[CH:2]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 238005Methyl 2-aminothiazole-5-carboxylateHCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 86665086Methyl 2-(4-(pyridin-3-yl)benzylamino)thiazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.8 mmol), methyl 2-aminothiazole-5-carboxylate (3.45 g, 21.83 mmol) and acetic acid (0.375 ml, 6.55 mmol) in toluene (109 ml). The reaction mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled to room temperature, and the volatiles were removed by rotary evaporation. Methanol was added, the solution was cooled to 0° C., and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The reaction was stirred at 0° C. for 15 minutes and allowed to warm to room temperature while stirring for an additional 2 hour. The solids were filtered off, washed with water and dried under high vacuum to give the title compound which was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under Dean-Stark conditions for 3 hours
  3. customthe volatiles were removed by rotary evaporation
  4. additionMethanol was added
  5. temperaturethe solution was cooled to 0° C.
  6. temperatureto warm to room temperature
  7. stirringwhile stirring for an additional 2 hour
  8. filtrationThe solids were filtered off
  9. washwashed with water
  10. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c66c9fb567dc416e8910a24320d80ad9
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334264B2

Verknüpfte Notizen

Wird geladen…