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

HRID 2178883노트

반응식

HRID 2178883 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8caa2e187f984313a4773c041968619d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067937B2

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