Diisopropylethylamine → 2-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17405

반응식

HRID 17405 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:24]([CH:27]([CH3:29])C)[CH2:25]C)(C)C.Cl.N1CCC1>ClCCl.C(O)C>[N:24]1([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:10]=3[F:11])[N:6]=2)[CH2:25][CH2:29][CH2:27]1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 12308726Azetidine hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685856232-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 74%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-130) (0.11 g, 0.38 mmol) was dissolved in a mixed solvent of dichloromethane (10 ml) and ethanol (7 ml), then diisopropylethylamine (0.21 ml, 1.23 mol) and azetidine hydrochloride (71.5 mg, 0.76 mmol) were added. After stirring at an external temperature of about 60° C. for 3 hours, the reaction liquid was concentrated under reduced pressure and diluted with dichloromethane. After washing with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1) to obtain a colorless solid (85 mg, 74%).

후처리

  1. customthe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additiondiluted with dichloromethane
  4. washAfter washing with water
  5. dry with materialdrying over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1)

출처 및 근거

ORD 기록
ord-82c3a8fc81a14a919363875a9edbf55d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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