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

HRID 17402
ノート
印刷プレビュー

反応式

HRID 17402 の反応式
F[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([CH3:16])[C:5]([C:14]#[N:15])=[C:6]2[C:10]=1[O:9][C:8]([N:11]([CH3:13])[CH3:12])=[N:7]2.C(N(CC)CC)C.[CH3:30][N:31]([CH3:37])[C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1>CS(C)=O.ClCCl>[CH3:12][N:11]([CH3:13])[C:8]1[O:9][C:10]2[C:6](=[C:5]([C:14]#[N:15])[C:4]([CH3:16])=[C:3]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:2]=2[N:34]2[CH2:35][CH2:36][C@H:32]([N:31]([CH3:37])[CH3:30])[CH2:33]2)[N:7]=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 685846257-Fluoro-2-(dimethylamino)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 510393142-(dimethylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 33%

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-2-(dimethylamino)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-132) (0.18 g, 0.61 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.17 ml, 1.23 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 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 (dichloromethane:methanol=30:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a pale beige solid (78.5 mg, 33%).

後処理

  1. washwashed with water and 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 (dichloromethane:methanol=30:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

出典と根拠

ORDレコード
ord-b45f8c6ea219484faa12f8677fab6b29
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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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート