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

HRID 40781

반응식

HRID 40781 반응식
[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]=[CH: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[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=3)[CH2:48][CH2:49]2)=[O:7])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 944591-(2-Pyridyl)piperazineHCID 533741991-(4-Methylbenzamido)-2-(chloroacetamido)-anthraquinone

생성물 1

HCID 533748811-(4-Methylbenzamido)-2-[2-[4-(2-pyridyl)piperazino]acetylamino]-anthraquinone수율 63%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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-pyridyl)piperazine (1.21 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 earth orange compound CC-49. Mol. Wt.: 559.6145 (C33H29N5O4); Rf: 0.28 (ethyl acetate:n-hexane=1:2); Yield: 63%; Mp.: 258-259° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 559.2220 (C33H29N5O4+). Found, 559.2224. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.16 (s, 3H, —CH3), 3.05 (br, 8H, —CH2—), 3.22 (s, 2H, —CH2N—), 6.54 (d, J=8.4 Hz, 1H, Ar—H), 6.66 (t, J=6.3 Hz, 1H, Ar—H), 7.08 (d, J=7.8 Hz, 2H, Ar—H), 7.52 (td, J=7.7 Hz, J=2.1 Hz, 1H, Ar—H), 7.87-7.91 (m, 2H, Ar—H), 7.97 (d, J=8.1 Hz, 2H, Ar—H), 8.07-8.19 (m, 2H, Ar—H), 8.29 (d, =8.7 Hz, 1H, Ar—H), 8.82 (d, J=9.0 Hz, 1H, Ar—H), 10.16 (s, 1H, Ar—NH—), 10.51 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 20.88, 44.21, 52.56, 61.54, 107.00, 113.11, 124.91, 126.42, 126.89, 126.99, 127.63, 128.03, 128.21, 129.01, 129.29, 132.26, 133.39, 134.19, 134.52, 134.58, 137.30, 140.73, 142.51, 147.49, 159.15, 166.26, 166.31 (NCO), 169.23 (NCO), 181.54 (CO), 183.63 (CO).

후처리

  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 earth orange compound CC-49

출처 및 근거

ORD 기록
ord-189370686ab7484f89201c2cbe4bc7f3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530465B2

연결된 노트

불러오는 중…