Diisopropylethylamine → 7-Fluoro-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17483노트

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HRID 17483 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(CC)C(C)C)(C)C.[OH:30][C:31]1([CH3:35])[CH2:34][NH:33][CH2:32]1>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:33]1[CH2:34][C:31]([OH:30])([CH3:35])[CH2:32]1)=[N:6]2

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 115427823-Methylazetidin-3-olHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685846307-Fluoro-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 92.1%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
100 °C

실험 절차

Under nitrogen atmosphere, 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (216 mg, 0.753 mmol) was dissolved in N,N-dimethylsulfoamide (10 ml), then N,N-diisopropylethylamine (584 μl, 3.35 mmol) and 3-hydroxy-3-methylazetidine (132 mg, 1.51 mmol) dissolved in N,N-dimethylsulfoamide (5 ml) were added, followed by stirring under heat at 100° C. for 20 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 (234 mg, 92%) as a white solid.

후처리

  1. additionwere added
  2. temperatureAfter cooling
  3. washwashing with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium, sulfate
  5. customthe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-21675023213a4610ba4c4e9da763fe5f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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