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

HRID 2178883Notes

Reaction equation

HRID 2178883 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-8caa2e187f984313a4773c041968619d
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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