Reaktion #595359

ord-206d5f9573b14e588299a90eced54041

Reaktionsgleichung

CC1(C)OC[C@@H](COc2ccc(-c3c(C#N)c(N)nc(SCc4coc(-c5ccc(Cl)cc5)n4)c3C#N)cc2)O1
compound
CC1(C)OC[C@@H](COc2ccc(-c3c(C#N)c(N)nc(SCc4coc(-c5ccc(Cl)cc5)n4)c3C#N)cc2)O1
2-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-phenyl)pyridine-3,5-dicarbonitrile
O
water
N#Cc1c(N)nc(SCc2coc(-c3ccc(Cl)cc3)n2)c(C#N)c1-c1ccc(OC[C@@H](O)CO)cc1
2-Amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-(4-{[(2S)-2,3-dihydroxypropyl]oxy}phenyl)pyridine-3,5-dicarbonitrile

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter concentration of the reaction mixture on a rotary evaporator
  2. 2
    Sonstigethe residue is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  3. 3
    SonstigeAfter removal of the solvent
  4. 4
    Sonstigeon a rotary evaporator
  5. 5
    Sonstigethe product is obtained as a white solid

Vorschrift

400 mg (0.70 mmol) of the compound from Example 46A are initially charged in 17 ml of acetic acid, and 8.6 ml of water are then added carefully. The mixture is stirred at RT for 12 h. After concentration of the reaction mixture on a rotary evaporator, the residue is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). After removal of the solvent on a rotary evaporator, the product is obtained as a white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09095582B2uspto-grants-2015_08