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Diethyl Malonate → 2-{5-[2-(4-Acetylamino-phenylsulfanyl)-5-methyl-phenylamino]-[1,8]naphthyridin-2-yl}-malonic acid diethyl ester

HRID 2358571
ノート
印刷プレビュー

反応式

HRID 2358571 の反応式
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:15]1[N:24]=[C:23]2[C:18]([C:19]([NH:25][C:26]3[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=3[S:33][C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:43])[CH3:42])=[CH:36][CH:35]=3)=[CH:20][CH:21]=[N:22]2)=[CH:17][CH:16]=1>C1COCC1>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([C:15]1[CH:16]=[CH:17][C:18]2[C:23](=[N:22][CH:21]=[CH:20][C:19]=2[NH:25][C:26]2[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=2[S:33][C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:43])[CH3:42])=[CH:36][CH:35]=2)[N:24]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 86615485N-{4-[2-(7-Chloro-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenyl}-acetamide

生成物 1

HCID 672508532-{5-[2-(4-Acetylamino-phenylsulfanyl)-5-methyl-phenylamino]-[1,8]naphthyridin-2-yl}-malonic acid diethyl ester収率 84%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a slurry of sodium hydride (95%, 0.045 g, 1.8 mmol) in 10 mL anhydrous THF at 0° C. under an atmosphere of N2 was added diethyl malonate (0.32 g, 2.0 mmol) dropwise. The mixture was stirred for 30 minutes at ambient temperature, treated with the product from Example 24a (0.141 g, 0.3 mmol), heated at 110° C. for two hours, cooled and partitioned between EtOAc and water. The ethyl acetate layer washed with saturated brine, dried over sodium sulfate, filtered and concentrated giving the title compound as a yellow glass, (0.14 g, 84% yield).

後処理

  1. temperatureheated at 110° C. for two hours
  2. temperaturecooled
  3. custompartitioned between EtOAc and water
  4. washThe ethyl acetate layer washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f495f410fdb24f98acf270452d864f3c
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07763731B2

反応ノート

読み込み中…

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