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

HRID 883883ノート

反応式

HRID 883883 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

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 8028Tetrahydrofuran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 23a (0.141 g, 0.3 mmol), heated at 110° C. for two hours, cooled and partitioned between EtOAc and water. The ethyl acetate layer was 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 was 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-2a213fc6d9d34945ba2df2ec8b630909
出典データセット
uspto-grants-2012_08
特許番号
US08236950B2

反応ノート

読み込み中…