Reacción #69054

Ecuación de reacción

ethyl acetate

DIPEA

1,4-dioxa-8-azaspiro[4.5]decane

CC-12

1-(4-methylbenzamido)-2-(chloroacetamido)-anthraquinone

→

1-(4-methylbenzamido)-2-[2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)acetylamino]-anthraquinone

Rendimiento 55.0%

Disolventes

EtOH

n-hexane

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThis mixture was heated
2. 2
   Temperaturaunder reflux for 16 hours
3. 3
   OtroAfter the completion of the reaction
4. 4
   Filtraciónthe mixture was filtered
5. 5
   Concentraciónthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
6. 6
   ExtracciónThe residue was extracted with ethyl acetate for several times
7. 7
   OtroThe extract was dried on magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   LavadoThe crude product was washed with ethyl acetate/hexane
10. 10
    OtroFinally, the crude product was recrystallized in hot ethanol
11. 11
    Otroto obtain a brown compound CC-40

Procedimiento

Compound CC-12 (0.86 g, 2 mmole) was dissolved in anhydrous tetrahydrofuran (30 ml), and to the solution was added successively with DIPEA (1 ml, 6 mmole) and 1,4-dioxa-8-azaspiro[4.5]decane (1.03 ml, 8 mmole) under stirring for 5 to 10 minutes. This mixture was heated under reflux for 16 hours. After the completion of the reaction, the mixture was filtered, and the filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator). The residue was extracted with ethyl acetate for several times. The extract was dried on magnesium sulfate, and concentrated under reduced pressure. The crude product was washed with ethyl acetate/hexane. Finally, the crude product was recrystallized in hot ethanol to obtain a brown compound CC-40. Mol. Wt.: 539.5785 (C31H29N3O6); Rf: 0.34 (ethyl acetate:n-hexane=1:2); Yield: 55%; Mp.: 197-198° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 539.2056 (C31H29N3O6+). Found, 539.2051. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 1.39 (d, J=5.4 Hz, 8H, —CH2—), 2.43 (s, 3H, —CH3), 3.15 (s, 2H, —CH2N—), 3.77 (s, 4H, —CH2—), 7.41 (d, J=7.8 Hz, 1H, Ar—H), 7.88-7.91 (m, 2H, Ar—H), 8.06 (d, J=8.1 Hz, 2H, Ar—H), 8.10-8.19 (m, 2H, Ar—H), 8.26 (d, J=8.7 Hz, 1H, Ar—H), 8.70 (d, J=8.7 Hz, 1H, Ar—H), 10.03 (s, 1H, Ar—NH—), 10.60 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 20.88, 33.68, 51.35, 61.29, 63.34, 63.52, 105.58, 125.90, 126.28, 126.32, 126.91, 127.75, 127.86, 128.18, 129.18, 129.40, 130.44, 132.29, 134.13, 134.38, 134.44, 140.32, 142.46, 166.29 (NCO), 169.31 (NCO), 181.44 (CO), 183.81 (CO).

Fuente