Diisopropylethylamine → 7-Fluoro-2-[3-(hydroxymethyl)azetidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17481노트

반응식

HRID 17481 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.[OH:30][CH2:31][CH:32]1[CH2:35][NH:34][CH2:33]1>C(Cl)Cl.C(Cl)(Cl)Cl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:34]1[CH2:35][CH:32]([CH2:31][OH:30])[CH2:33]1)=[N:6]2

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 13400658(Azetidin-3-yl)methanolHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685843917-Fluoro-2-[3-(hydroxymethyl)azetidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 74%

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) (240 mg, 0.84 mmol) was dissolved in methylene chloride (10 ml), then diisopropylethylamine (584 μl, 3.35 mmol) and 3-hydroxymethylazetidine (206 mg, 1.67 mmol) dissolved in methylene chloride (5 ml) were added, followed by heating under reflux in a sealed tube for 5 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. The eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (208 mg, 74%) as a white solid.

후처리

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux in a sealed tube for 5 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-11a959f190a0418f82f8c70cb8972444
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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