Anisole → 5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol

HRID 911058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911058
COC1C=CC(C[S:8][C:9]2[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]3[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:21]=3)[CH:10]=2)=CC=1.C1(OC)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[Br:15][C:14]1[C:9]([SH:8])=[CH:10][C:11]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:21]=2)=[N:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 866347724-(4-methoxybenzylthio)-5-bromo-N-(4-phenethylthiazol-2-yl)pyridine-2-amine

Produkt 1

HCID 1785277275-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiolAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

4-(4-methoxybenzylthio)-5-bromo-N-(4-phenethylthiazol-2-yl)pyridine-2-amine (1.23 g, 2.4 mmol) was dissolved in TFA (10 mL):anisole (2 mL) (5:1). The reaction mixture was stirred at 75° C. overnight, then neutralized with solid NaHCO3, extracted with EtOAc, dried, and concentrated. The crude material was triturated in MeOH and filtered. The filtrate was further concentrated and triturated again with MeOH. The solids were combined and dried to give the desired product (0.68 g, 72% yield).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was triturated in MeOH
  5. filtrationfiltered
  6. concentrationThe filtrate was further concentrated
  7. customtriturated again with MeOH
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a0b7f573027c4478b41296cc46429dfd
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

Notizen zur Reaktion

Wird geladen…