3-Oxabicyclo(3.1.0)hexane-2,4-dione → HCID 66801595, compound

HRID 2366305Notes

Reaction equation

HRID 2366305 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][C:11]2[C:12]([NH2:18])=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1.[CH:19]12[CH2:24][CH:23]1[C:22](=[O:25])[O:21][C:20]2=O>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[S:10][C:11]2[C:12]([N:18]3[C:20](=[O:21])[CH:19]4[CH:23]([CH2:24]4)[C:22]3=[O:25])=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 66801618HCID 66801618, compound

Product 1

HCID 66801595HCID 66801595, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridin-4-amine (550 mg, 1.86 mmol) and 3-oxabicyclo[3.1.0]hexane-2,4-dione (835 mg, 7.46 mmol) in 1,4-dioxane (10 mL) was heated at 90° C. for 2 hours. The reaction mixture was then cooled to room temperature and concentrated. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:10 to 1:2) to give the desired product as a solid. (570 mg, 78.8% yield). LCMS (ESI) m/z: 390.0 [M+H+].

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography
  3. washeluting with ethyl acetate/petroleum ether (1:10 to 1:2)

Sources & evidence

ORD record
ord-0443a3928d574a8fab25b510a579f5d9
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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