Réaction #69054

Équation de réaction

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

Rendement 55.0%

Solvants

EtOH

n-hexane

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureThis mixture was heated
2. 2
   Températureunder reflux for 16 hours
3. 3
   AutreAfter the completion of the reaction
4. 4
   Filtrationthe mixture was filtered
5. 5
   Concentrationthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
6. 6
   ExtractionThe residue was extracted with ethyl acetate for several times
7. 7
   AutreThe extract was dried on magnesium sulfate
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   LavageThe crude product was washed with ethyl acetate/hexane
10. 10
    AutreFinally, the crude product was recrystallized in hot ethanol
11. 11
    Autreto obtain a brown compound CC-40

Mode opératoire

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).

Source