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Water → Methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydroimidazo[4,5-a]quinolizine-10-carboxylate

HRID 378684
ノート
印刷プレビュー

反応式

HRID 378684 の反応式
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][NH:7][C:6](=S)[C:5]=2[N:4]=[CH:3]1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22](C2OC2(C#N)C#N)[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:33]([O:37][CH3:38])(=[O:36])[C:34]#[CH:35].[OH2:39].CN1[CH2:45][CH2:44]N(C)C1=O>>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:44]2[C:6](=[O:39])[N:7]3[C:35](=[C:34]([C:33]([O:37][CH3:38])=[O:36])[CH:45]=2)[C:5]2[N:4]=[CH:3][N:2]([CH3:1])[C:10]=2[CH:9]=[CH:8]3)=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 962WaterHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 13536Methyl propiolateHCID 193535981-Methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thioneHCID 193536803-(3-Benzyloxyphenyl)-oxirane-2,2-dicarbonitrile

生成物 1

HCID 19353647Methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydroimidazo[4,5-a]quinolizine-10-carboxylate
収率 34%

実験手順

3.50 g (21.2 mmol) of 1-methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione were dissolved in 0.6 1 of 1,3-dimethyl-2-imidazolidinone at 140° C., left to cool to room temperature, treated with 5.9 g (21.4 mmol) of 3-(3-benzyloxyphenyl)-oxirane-2,2-dicarbonitrile and stirred over the weekend. Then, 7.8 ml of methyl propiolate were added and the mixture was stirred at 110° C. for 22 hours. After cooling the solution was stirred into 6 l of water, the precipitate was filtered off and it was chromatographed over silica gel with dichloromethane/acetone/hexane 2:1:1. There were obtained 3.20 g (34%) of methyl 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylate as yellow crystals with m.p 196-198° C.

後処理

  1. waitleft
  2. stirringthe mixture was stirred at 110° C. for 22 hours
  3. temperatureAfter cooling the solution
  4. filtrationthe precipitate was filtered off
  5. customit was chromatographed over silica gel with dichloromethane/acetone/hexane 2:1:1

出典と根拠

ORDレコード
ord-b1d83a724eb54fa48832509d7bfe2870
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06030984

反応ノート

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