تفاعل #595354

ord-d42f07e795de498085f626ce02079b8a

معادلة التفاعل

C[C@@H](COc1ccc(-c2c(C#N)c(N)nc(S)c2C#N)cc1)O[Si](C)(C)C(C)(C)C
compound
C[C@@H](COc1ccc(-c2c(C#N)c(N)nc(S)c2C#N)cc1)O[Si](C)(C)C(C)(C)C
2-Amino-4-(4-{[(2S)-2-{[tert-butyl(dimethyl)silyl]oxy}propyl]oxy}phenyl)-6-mercaptopyridine-3,5-dicarbonitrile
Cc1oc(-c2ccc(F)cc2)nc1CCl
4-(chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazole
O=C([O-])O.[Na+]
sodium bicarbonate
Cc1oc(-c2ccc(F)cc2)nc1CSc1nc(N)c(C#N)c(-c2ccc(OC[C@H](C)O[Si](C)(C)C(C)(C)C)cc2)c1C#N
product
Cc1oc(-c2ccc(F)cc2)nc1CSc1nc(N)c(C#N)c(-c2ccc(OC[C@H](C)O[Si](C)(C)C(C)(C)C)cc2)c1C#N
2-Amino-4-(4-{[(2S)-2-{[tert-butyl(dimethyl)silyl]oxy}propyl]oxy}phenyl)-6-({[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]methyl}thio)pyridine-3,5-dicarbonitrile

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe mixture is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  2. 2
    أخرىRemoval of the solvent
  3. 3
    أخرىon a rotary evaporator

الإجراء التجريبي

100 mg (0.18 mmol) of the compound from Example 7A, 45 mg (0.20 mmol) of 4-(chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazole and 46 mg (0.55 mmol) of sodium bicarbonate in 2 ml of dry DMF are stirred at RT for 20 h. The mixture is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gives the product as a white solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09095582B2uspto-grants-2015_08