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

HRID 17410ノート

反応式

HRID 17410 の反応式
F[C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]2[C:10]=1[O:9][C:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[N:7]2.C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1>CS(C)=O.ClCCl>[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][N:37]([C:2]2[C:3]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]3[C:10]=2[O:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:7]3)[CH2:36]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685852407-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685846837-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile収率 44.3%

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

7-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile (I-136) (0.21 g, 0.63 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.91 ml, 1.37 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.16 ml, 1.26 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 silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1) and preparative thin-layer chromatography (dichloromethane:methanol=20:1), then isopropyl ether was added, and the insoluble matter was collected by filtration to obtain a beige solid (0.12 g, 44%).

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 silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1)
  5. additionisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

出典と根拠

ORDレコード
ord-a0b99ea381194955b0ae122e9c868949
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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