Reaktion #329352

Reaktionsgleichung

4-fluorophenylthiourea

1,3-dichloroacetone

compound

2′-Amino-6-[(2-hydroxyethyl)amino]-6′-mercapto-3,4′-bipyridine-3′,5′-dicarbonitrile

sodium bicarbonate

→

2′-Amino-6′-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]-6-[(2-hydroxyethyl)amino]-3,4′-bipyridine-3′,5′-dicarbonitrile

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   workup.STIRRINGthe mixture is stirred at RT for a further 20 h
3. 3
   FiltrationThe mixture is then filtered through a paper
4. 4
   Filtrationfilter
5. 5
   Sonstigethe filtrate is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
6. 6
   workup.ADDITIONSat. sodium bicarbonate solution (5 ml) is added to the product fraction
7. 7
   Sonstigeobtained
8. 8
   Extraktionthe mixture is extracted with ethyl acetate (three times, 5 ml each)
9. 9
   TrocknenThe combined organic phases are dried over magnesium sulphate
10. 10
    Sonstigethe solvent is removed on a rotary evaporator

Vorschrift

18 mg (0.10 mmol) of 4-fluorophenylthiourea and 13 mg (0.10 mmol) of 1,3-dichloroacetone are dissolved in 2 ml of DMF, and the reaction solution is stirred at 80° C. for 3 h. After cooling, 89 mg (0.09 mmol, 33% pure) of the compound from example 4A and 32 mg (0.38 mmol) of sodium bicarbonate are added, and the mixture is stirred at RT for a further 20 h. The mixture is then filtered through a paper filter, and the filtrate is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Sat. sodium bicarbonate solution (5 ml) is added to the product fraction obtained, and the mixture is extracted with ethyl acetate (three times, 5 ml each). The combined organic phases are dried over magnesium sulphate, and the solvent is removed on a rotary evaporator.

Quelle