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

HRID 17408
ノート
印刷プレビュー

反応式

HRID 17408 の反応式
F[C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]2[C:10]=1[O:9][C:8]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[N:7]2.C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1>CS(C)=O.ClCCl>[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][N:36]([C:2]2[C:3]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]3[C:10]=2[O:9][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:7]3)[CH2:35]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685847937-Fluoro-5-methyl-6-phenyl-2-(pyrrolidin-1-yl)-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 510393167-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(pyrrolidin-1-yl)-1,3-benzoxazole-4-carbonitrile収率 29.5%

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

7-Fluoro-5-methyl-6-phenyl-2-(pyrrolidin-1-yl)-1,3-benzoxazole-4-carbonitrile (I-135) (0.10 g, 0.31 mmol) was suspended in dimethyl sulfoxide (3.5 ml), then triethylamine (90.0 μl, 0.65 mmol) and (3S)-3-(dimethylamino)pyrrolidine (88.0 μl, 0.69 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 ether and a small amount of hexane were added, and the insoluble matter was collected by filtration to obtain a beige solid (38 mg, 29%).

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. additionether and a small amount of hexane were added
  6. filtrationthe insoluble matter was collected by filtration

出典と根拠

ORDレコード
ord-3ad14fca122b42588bc33ae949e6f99e
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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