Реакция #1583817

ord-210e112c9e3943e5a593e0ca7177feb1

Уравнение реакции

O=S(=O)(O)O
sulphuric acid
CCc1nc(-c2ccc(F)cc2)c(-c2ccnc(NCc3ccccc3)c2)s1
N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine
[Na+].[OH-]
sodium hydroxide
CCc1nc(-c2ccc(F)cc2)c(-c2ccnc(N)c2)s1
4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Экстракцияthe mixture is extracted with dichloromethane (3×100 ml)
  2. 2
    СушкаThe combined organic phases are dried over MgSO4
  3. 3
    ДругоеThe residue is triturated with MTBE
  4. 4
    Фильтрацияfiltered off
  5. 5
    ДругоеThe product obtained

Методика

With ice cooling, 23 ml of conc. sulphuric acid are added to 4.75 g (10.9 mmol) of N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine, and the reaction mixture is stirred at room temperature for 30 min. The reaction mixture is stirred into 100 ml of ice-water, the pH is adjusted to 10 using concentrated aqueous sodium hydroxide solution and the mixture is extracted with dichloromethane (3×100 ml). The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. The residue is triturated with MTBE and filtered off. The product obtained is 2.80 g (82%) of a beige solid; log P (pH2.7): 1.29 with MS (ESI): 300.1 ([M+H]+).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09198426B2uspto-grants-2015_12