Acetic Acid → 2-(4,6-Dichloro-1,5-naphthyridin-3-yl)-2-oxoethyl acetate

HRID 2178883ノート

反応式

HRID 2178883 の反応式
[C:1]([OH:4])(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[CH2:15][C:16]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[Cl:28])=[N:25][C:24]([Cl:29])=[CH:23][CH:22]=2)=[O:17]>CC(C)=O>[C:1]([O:4][CH2:15][C:16]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[Cl:28])=[N:25][C:24]([Cl:29])=[CH:23][CH:22]=2)=[O:17])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 897054772-Chloro-1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone

生成物 1

HCID 897051652-(4,6-Dichloro-1,5-naphthyridin-3-yl)-2-oxoethyl acetate収率 42%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of acetic acid (0.32 mL, 5.5 mmol) and N,N-diisopropylethylamine (0.87 mL, 5.0 mmol) in acetone (20 mL) was added 2-chloro-1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (0.26 g, 0.96 mmol) and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with satd. aq. sodium bicarbonate and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/ethyl acetate) to afford the desired product (0.12 g, 42%) as a white solid. ESI MS m/z 299 [M+H]+.

後処理

  1. additionThe reaction mixture was diluted with satd
  2. extractionaq. sodium bicarbonate and extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-8caa2e187f984313a4773c041968619d
出典データセット
uspto-grants-2015_06
特許番号
US09067937B2

反応ノート

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