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

HRID 526162Notes

Reaction equation

HRID 526162 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-44bc67d9ed494a889a07d9e9fc48149e
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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