Ethyl Acetate → 1-(4-Methylbenzamido)-2-[2-[4-(2-pyrimidinyl)piperazino]acetylamino]-anthraquinone

HRID 40782

Reaktionsgleichung

Reaktionsgleichung von HRID 40782
[CH3:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][C:9]2[C:22]3[C:21](=[O:23])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:24])[C:13]=3[CH:12]=[CH:11][C:10]=2[NH:25][C:26](=[O:29])[CH2:27]Cl)=[O:7])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[N:41]1[CH:46]=[CH:45][CH:44]=[N:43][C:42]=1[N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.C(OCC)(=O)C>O1CCCC1.CCO.CCCCCC>[CH3:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][C:9]2[C:22]3[C:21](=[O:23])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:24])[C:13]=3[CH:12]=[CH:11][C:10]=2[NH:25][C:26](=[O:29])[CH2:27][N:50]2[CH2:51][CH2:52][N:47]([C:42]3[N:41]=[CH:46][CH:45]=[CH:44][N:43]=3)[CH2:48][CH2:49]2)=[O:7])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 533741991-(4-Methylbenzamido)-2-(chloroacetamido)-anthraquinone

Produkt 1

HCID 533748821-(4-Methylbenzamido)-2-[2-[4-(2-pyrimidinyl)piperazino]acetylamino]-anthraquinoneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

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-(2-pyrimidyl)piperazine (1.13 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 kelly green compound CC-50. Mol. Wt.: 560.6025 (C32H28N6O4), Rf: 0.32 (ethyl acetate:n-hexane=1:2); Yield: 41%; Mp.: 267-268° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 560.2172 (C32H28N6O4+). Found, 560.2170. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.20 (s, 3H, —CH3), 3.05 (br, 8H, —CH2—), 3.11 (s, 2H, —CH2N—), 3.22 (br, 8H, —CH2—), 6.66 (d, J=4.8 Hz, 1H, Ar—H), 7.16 (d, J=7.8 Hz, 1H, Ar—H), 7.87-7.91 (m, 2H, Ar—H), 8.01 (d, J=6.0 Hz, 2H, Ar—H), 8.08-8.19 (m, 2H, Ar—H), 8.32 (d, =7.2 Hz, 1H, Ar—H), 8.82 (d, J=8.7 Hz, 1H, Ar—H), 10.19 (s, 1H, Ar—NH—), 10.54 (s, 1H, Ar—NH—); 13C-NMR (125 MHz, DMSO-d6) δ (ppm): 20.98, 42.53, 43.01, 52.46, 61.44, 110.28, 111.11, 124.77, 126.32, 126.89, 127.44, 127.92, 128.14, 128.90, 129.18, 130.18, 132.26, 134.06, 134.48, 142.39, 157.65, 158.07, 161.24, 166.12, (NCO), 169.08 (NCO), 181.35 (CO), 183.39 (CO).

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customAfter the completion of the reaction
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
  6. extractionThe residue was extracted with ethyl acetate for several times
  7. customThe extract was dried on magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe crude product was washed with ethyl acetate/hexane
  10. customFinally, the crude product was recrystallized in hot ethanol
  11. customto obtain a kelly green compound CC-50

Quellen und Nachweise

ORD-Eintrag
ord-e3197e26f5044da28f1de791ac0524e1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530465B2

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