Реакция #595355

ord-f4796a77080c48e29be5b974089af764

Уравнение реакции

O
water
CC(C)(C)[O-].[K+]
potassium tert-butoxide
OCc1coc(-c2ccc(Cl)cc2)n1
compound
OCc1coc(-c2ccc(Cl)cc2)n1
[2-(4-Chlorophenyl)-1,3-oxazol-4-yl]methanol
CC1(C)OC[C@H](COc2ccc(-c3c(C#N)c(N)nc(Sc4ccccc4)c3C#N)cc2)O1
compound
CC1(C)OC[C@H](COc2ccc(-c3c(C#N)c(N)nc(Sc4ccccc4)c3C#N)cc2)O1
2-Amino-4-(4-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-phenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile
CC1(C)OC[C@H](COc2ccc(-c3c(C#N)c(N)nc(OCc4coc(-c5ccc(Cl)cc5)n4)c3C#N)cc2)O1
2-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-(4-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}phenyl)pyridine-3,5-dicarbonitrile

Растворители

Условия реакции

Температура
60°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураafter cooling, at RT for a further 10 h
  2. 2
    ДругоеThe precipitate formed
  3. 3
    Фильтрацияis filtered off with suction
  4. 4
    Промывкаwashed once with about 2 ml of cold water
  5. 5
    ДругоеThis is followed by purification by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Методика

122 mg (1.09 mmol) of potassium tert-butoxide are suspended in 2 ml of dry 1,2-dimethoxyethane. 229 mg (1.09 mmol) of the compound from Example 100A and 100 mg (0.22 mmol) of the compound from Example 98A are then added successively. The reaction mixture is stirred at 60° C. for 2 h and, after cooling, at RT for a further 10 h. 5 ml of water are then added to the mixture. The precipitate formed is filtered off with suction and washed once with about 2 ml of cold water. This is followed by purification by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09095582B2uspto-grants-2015_08