Ethyl Acetate → 1-(4-Methylbenzamido)-2-[2-[(1,3-dioxolan-2-ylmethyl)(methyl)amino]acetylamino]-anthraquinone

HRID 40773

반응식

HRID 40773 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.[CH3:41][NH:42][CH2:43][CH:44]1[O:48][CH2:47][CH2:46][O:45]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:42]([CH2:43][CH:44]2[O:48][CH2:47][CH2:46][O:45]2)[CH3:41])=[O:7])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 5417541,3-Dioxolane-2-methanamine, N-methyl-HCID 533741991-(4-Methylbenzamido)-2-(chloroacetamido)-anthraquinone

생성물 1

HCID 533745861-(4-Methylbenzamido)-2-[2-[(1,3-dioxolan-2-ylmethyl)(methyl)amino]acetylamino]-anthraquinone수율 43%

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 2-methylaminomethyl-1,3 dioxolane (0.91 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-36. Mol. Wt.: 513.5412 (C29H27N3O6); Rf: 0.31 (ethyl acetate: n-hexane=1:2); Yield: 43%; Mp.: 156-157° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 513.1900 (C29H27N3O6+). Found, 513.1902. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.18 (s, 3H, —CH3), 2.44 (s, 3H, —CH3), 2.54 (d, J=8.7 Hz, 2H, —NCH2—), 3.26 (s, 2H, —CH2N—), 3.52-3.55 (m, 2H, —OCH2—), 3.72-3.77 (m, 2H, —OCH2—), 4.58 (t, J=4.5 Hz, 1H, —OCHO—), 7.43 (d, J=7.8 Hz, 2H, Ar—H), 7.88-7.92 (m, 2H, Ar—H), 8.04 (d, J=8.1 Hz, 2H, Ar—H), 8.10-8.19 (m, 2H, Ar—H), 8.27 (d, J=8.4 Hz, 1H, Ar—H), 8.70 (d, J=8.7 Hz, 1H, Ar—H), 10.15 (s, 1H, Ar—NH—), 10.53 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 20.87, 43.49, 59.43, 61.73, 63.91, 102.61, 125.50, 126.31, 126.48, 126.90, 127.89, 128.06, 129.06, 129.31, 130.75, 132.33, 134.16, 134.38, 134.45, 140.42, 142.29, 166.25 (NCO), 169.59 (NCO), 181.46 (CO), 183.70 (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 kelly green compound CC-36

출처 및 근거

ORD 기록
ord-d35826ad94ef4ebe87ea18c01de95dde
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530465B2

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