Water → N-[3-Benzyl-5-(4-methoxyphenyl)pyrazin-2-yl]-6-methoxy-N-(6-methoxy-1-naphthoyl)-1-naphthamide

HRID 333632

반응식

HRID 333632 반응식
[CH2:1]([C:8]1[C:9]([NH2:22])=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35](Cl)=[O:36])=[CH:30][CH:29]=[CH:28]2.[OH2:38]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([C:8]1[C:9]([N:22]([C:35]([C:31]2[C:32]3[C:27](=[CH:26][C:25]([O:24][CH3:23])=[CH:34][CH:33]=3)[CH:28]=[CH:29][CH:30]=2)=[O:38])[C:35]([C:31]2[C:32]3[C:27](=[CH:26][C:25]([O:24][CH3:23])=[CH:34][CH:33]=3)[CH:28]=[CH:29][CH:30]=2)=[O:36])=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 113007862-Amino-3-benzyl-5-(4-methoxyphenyl)pyrazineHCID 575166936-Methoxy-1-naphthoyl chloride

생성물 1

HCID 67432726N-[3-Benzyl-5-(4-methoxyphenyl)pyrazin-2-yl]-6-methoxy-N-(6-methoxy-1-naphthoyl)-1-naphthamide수율 68.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

반응 조건

온도
50 °C

실험 절차

Under an argon atmosphere, to a solution of 3-benzyl-5-(4-methoxyphenyl)pyrazin-2-amine (12) (synthesized by the process of M. Adamczyk, et al., Org. Prep. Proced. Int., 33, 477-485 (2001)) (500 mg, 1.72 mmol) in pyridine (5 mL) were successively added 4-(dimethylamino)pyridine (21.0 mg, 172 μmol) and 6-methoxy-1-naphthoyl chloride (22) prepared above at room temperature, and the mixture was heated with stirring at 50° C. 18 hours. After cooling to room temperature, to the mixture was added water and the product was extracted with dichloromethane (×3). The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residual pyridine was azeotropically removed with toluene (×3). The residue was successively purified twice by column chromatography (silica gel 50 g, dichloromethane/ethyl acetate=9/1, and silica gel 50 g, n-hexane/ethyl acetate=2/1) to give Compound 11z (775 mg, 1.17 mmol, <68.3%) as a brown foamy solid containing some impurities. Rf=0.21 (n-hexane/ethyl acetate=2/1); 1H NMR (400 MHz, DMSO-d6) δ 3.82 (s, 3H), 3.83 (s, 6H), 4.39 (s, 2H), 7.04-7.09 (AA′BB′, 2H), 7.15-7.23 (m, 6H), 7.26-7.31 (m, 1H), 7.34-7.41 (m, 4H), 7.63-7.69 (m, 2H), 7.75-7.80 (AA′BB′, 2H), 8.02-8.08 (m, 4H), 9.07 (s, 1H).

후처리

  1. customprepared above at room temperature
  2. temperaturethe mixture was heated
  3. custom18 hours
  4. temperatureAfter cooling to room temperature, to the mixture
  5. extractionthe product was extracted with dichloromethane (×3)
  6. extractionThe combined organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residual pyridine was azeotropically removed with toluene (×3)
  11. customThe residue was successively purified twice by column chromatography (silica gel 50 g, dichloromethane/ethyl acetate=9/1, and silica gel 50 g, n-hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-8afc8beb1f7840b8aba6c03887d2ef67
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883432B2

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