Reacción #595361

ord-af5c3545457848289bb8c6c391466a30

Ecuación de reacción

N#Cc1c(Cl)nc(SCc2coc(-c3ccc(Cl)cc3)n2)c(C#N)c1-c1ccc(OC[C@@H](O)CO)cc1
compound
N#Cc1c(Cl)nc(SCc2coc(-c3ccc(Cl)cc3)n2)c(C#N)c1-c1ccc(OC[C@@H](O)CO)cc1
2-Chloro-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}thio)-4-(4-{[(2S)-2,3-dihydroxypropyl]-oxy}phenyl)pyridine-3,5-dicarbonitrile
CNCC(=O)OC.Cl
methyl N-methylglycinate hydrochloride
CCN(CC)CC
triethylamine
COC(=O)CN(C)c1nc(SCc2coc(-c3ccc(Cl)cc3)n2)c(C#N)c(-c2ccc(OC[C@@H](O)CO)cc2)c1C#N
Methyl N-[6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}thio)-3,5-dicyano-4-(4-{[(2S)-2,3-dihydroxypropyl]oxy}-phenyl)pyridin-2-yl]-N-methylglycinate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent is then removed on a rotary evaporator
  2. 2
    Otrothe 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
    OtroAfter removal of the solvent
  4. 4
    Otroon a rotary evaporator
  5. 5
    Otrothe product is obtained as a white solid

Procedimiento

108 mg (0.20 mmol) of the compound from Example 103A are dissolved in 3 ml of dry DMF, and 54 mg (0.39 mmol) of methyl N-methylglycinate hydrochloride and 59 mg (0.59 mmol) of triethylamine are added. The reaction mixture is stirred at RT for 8 h. The solvent is then removed on a rotary evaporator and 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.

Fuente

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