Methanol → HCID 88365911, 화합물

HRID 1737215노트

반응식

HRID 1737215 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[N:13][OH:14])[CH3:12].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[N:26]1[C:30](Cl)=[N:29][N:28]([CH3:32])[C:27]1=[O:33].[CH3:34][O-:35].[Na+].CO>O1CCCC1.C(OCC)(=O)C>[CH3:34][O:35][C:30]1[N:26]([C:20]2[C:19]([CH2:18][O:14][N:13]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[CH3:12])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:25])[C:27](=[O:33])[N:28]([CH3:32])[N:29]=1

참가 물질

8

반응물 5

HCID 887MethanolHCID 24758Sodium hydrideHCID 3185661-(naphthalen-2-yl)ethan-1-one oximeHCID 10942334Sodium MethoxideHCID 218419724-[2-(bromomethyl)-6-methylphenyl]-5-chloro-2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

생성물 1

HCID 88365911HCID 88365911, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(2-naphthalenyl)ethanone oxime (492 mg, 2.65 mmol) in tetrahydrofuran (7.5 mL) cooled to 0° C. under a nitrogen atmosphere was added 95% NaH (69 mg, 2.88 mmol) and the mixture was stirred for 20 min. The title compound of Step E (700 mg, 2.21 mmol) was then added to the reaction and the mixture was stirred at room temperature for 3 h. Sodium methoxide as a 30% solution in methanol (1.3 mL, 6.63 mmol) was added and the reaction mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated ammonium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent) to give 306 mg of the title compound of Step F, a compound of the invention, as a golden oil. 1H NMR (CDCl3): δ 2.19 (s,3H), 2.32 (s,3H), 3.41 (s,3H), 3.89 (s,3H), 5.21 (AB q,2H), 7.30 (d,1H), 7.36-7.5 (m,4H), 7.8 (m,4H), 7.97 (s,1H).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 10 h
  4. washwashed with saturated ammonium chloride
  5. dry with materialThe organic phase was dried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent)

출처 및 근거

ORD 기록
ord-eba9c9ca04534a478b77d5dae7df4b53
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962436

반응 노트

불러오는 중…