Sodium hydride → HCID 73848365, 화합물

HRID 1737208노트

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HRID 1737208 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]=[CH:21][C:20]=1[N:25]1[C:29]([O:30][CH3:31])=[N:28][N:27]([CH3:32])[C:26]1=[O:33]>CN(C=O)C>[CH3:31][O:30][C:29]1[N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][O:14][N:13]=[C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH3:12])[C:26](=[O:33])[N:27]([CH3:32])[N:28]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 3185661-(naphthalen-2-yl)ethan-1-one oximeHCID 110338324-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

생성물 1

HCID 73848365HCID 73848365, 화합물수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 0.56 g (3.02 mmol) of 1-(2-naphthalenyl)ethanone oxime in 10 mL of DMF was added 0.13 g (3.28 mmol) of NaH. 0.75 (2.52 mmol) of the title compound of Step D was then added to the reaction and the mixture was stirred at room temperature for 3 h. The reaction mixture was washed successively with water and saturated NaCl and then extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel using 60% ethyl acetate/hexane as eluent to give 0.80 g (79% yield) of the title compound of Step E, a compound of the invention, as a solid melting at 91-94° C.

후처리

  1. washThe reaction mixture was washed successively with water and saturated NaCl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel using 60% ethyl acetate/hexane as eluent

출처 및 근거

ORD 기록
ord-bfa59fe4836a4827a5efe68e2fc92c2b
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962436

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