Reacción #595355

ord-f4796a77080c48e29be5b974089af764

Ecuación de reacción

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

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaafter cooling, at RT for a further 10 h
  2. 2
    OtroThe precipitate formed
  3. 3
    Filtraciónis filtered off with suction
  4. 4
    Lavadowashed once with about 2 ml of cold water
  5. 5
    OtroThis 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)

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095582B2uspto-grants-2015_08