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

HRID 17406ノート

反応式

HRID 17406 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-dd66c21ae78448029bbd4b0f2bc20496
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…