Diisopropylethylamine → Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate

HRID 17478노트

반응식

HRID 17478 반응식
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C(N(C(C)C)CC)(C)C.[NH:30]1[CH2:33][CH:32]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31]1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:19]([C:7]1[C:5]2[N:6]=[C:2]([N:30]3[CH2:33][CH:32]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31]3)[O:3][C:4]=2[C:10]([F:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH3:18])#[N:20]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 54328202HCID 54328202, 화합물

생성물 1

HCID 86630854Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate수율 76.3%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매2회

실험 절차

Under nitrogen atmosphere, 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (400 mg, 1.40 mmol) was dissolved in methylene chloride (15 ml), then diisopropylethylamine (537 μl, 3.08 mmol) and ethyl azetidine-3-acetate (503 mg, 2.80 mmol) dissolved in methylene chloride (5 ml) were added, followed by heating under reflux for 19 hours. After cooling, diluting with chloroform and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. From the eluate with ethyl acetate/hexane (1:1, v/v), the entitled compound (420 mg, 76%) was obtained as a colorless oil.

후처리

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux for 19 hours
  4. temperatureAfter cooling
  5. washwashing with water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-fbbd76cfa78b4e5fbe82126ff45f29a3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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