Réaction #61737

Équation de réaction

4-{4-[4-(4-Hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}benzoic acid

1-furoylpiperazine

EDCI

HOBt

→

[4-(Furan-2-carbonyl)-piperazin-1-yl]-(4-{4-[4-(4-hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}phenyl)methanone

Rendement 9.0%

Solvants

CH2Cl2

THF

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 2% NaOH (aq, 30 mL), water (30 mL)
2. 2
   SéchageThe organic layer was dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   Autrewas subjected to preparatory HPLC (30-80 acetonitrile/water gradient, 20 min)
6. 6
   ConcentrationThe desired fractions were concentrated
7. 7
   Autreto remove most of the acetonitrile
8. 8
   Extractionthe aqueous mixture was extracted with CH2Cl2/2% NaOH (aq)
9. 9
   SéchageThe organic layer was dried (Na2SO4)
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated

Mode opératoire

4-{4-[4-(4-Hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}benzoic acid (0.34 g, 0.86 mmol) was dissolved in THF (5 mL). To this solution was added 1-furoylpiperazine (0.170 g), EDCI (0.180 g), and HOBt (0.127 g). The mixture was stirred 12 h. The mixture was then diluted with CH2Cl2 (20 mL) and washed with 2% NaOH (aq, 30 mL), water (30 mL), and then brine (30 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The crude solid was subjected to preparatory HPLC (30-80 acetonitrile/water gradient, 20 min). The desired fractions were concentrated to remove most of the acetonitrile, and then the aqueous mixture was extracted with CH2Cl2/2% NaOH (aq). The organic layer was dried (Na2SO4), filtered, and concentrated to afford [4-(Furan-2-carbonyl)-piperazin-1-yl]-(4-{4-[4-(4-hydroxybutylsulfanyl)phenyl]pyrimidin-2-ylamino}phenyl)methanone (0.042 g, 9%): HPLC Retention Time; 10.07 min. (Method B) M+H=558.3.

Source