Triethylamine → 2-(azetidin-1-yl)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17406노트

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HRID 17406 반응식
[N:1]1([C:5]2[O:6][C:7]3[C:8](=[C:10]([C:22]#[N:23])[C:11]([CH3:21])=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=3F)[N:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:24]([N:26]([CH2:29]C)[CH2:27][CH3:28])C.[NH:31]1CC[CH2:33][CH2:32]1>CS(C)=O.ClCCl>[N:1]1([C:5]2[O:6][C:7]3[C:8](=[C:10]([C:22]#[N:23])[C:11]([CH3:21])=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=3[N:31]3[CH2:32][CH2:33][C@H:27]([N:26]([CH3:24])[CH3:29])[CH2:28]3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 685856232-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685846442-(azetidin-1-yl)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 17%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

2-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-134) (0.11 g, 0.36 mmol) was dissolved in dimethyl sulfoxide (3.5 ml), then triethylamine (0.10 ml, 0.72 mmol) and (3S)-3-dimethylamino)pyrrolidine (92.0 μl, 0.73 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a pale beige solid (23 mg, 17%).

후처리

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

출처 및 근거

ORD 기록
ord-dd66c21ae78448029bbd4b0f2bc20496
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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