Dimethylformamide → HCID 22049685, compound

HRID 1830926Notes

Reaction equation

HRID 1830926 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[N:12]=1.S(Cl)(Cl)=O.[CH3:26][N:27]([CH:29]=O)C.[CH2:31]1COCC1>>[N:27]1([C:16]([C:15]2[CH:14]=[C:13]([C:11]3[N:12]=[C:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[S:9][CH:10]=3)[CH:21]=[CH:20][CH:19]=2)=[O:18])[CH2:29][CH2:31][CH2:26]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 22049703HCID 22049703, compound

Product 1

HCID 22049685HCID 22049685, compound

Procedure

3-[2-(4-Methylpyridin-3-yl)-1,3-thiazol-4-yl]benzoic acid (238 mg) was suspended in THF (10 ml) and thionyl chloride (0.09 ml) and DMF (0.05 ml) were added. The mixture was heated under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure and re-dissolved in THF (10 ml). To this solution was added a solution of azetidine hydrochloride (0.54 g) dissolved in 1N NaOH (10 ml), and the mixture was stirred at room temperature for 30 min. The reaction mixture extracted with ethyl acetate and the organic layer was dried and concentrated. The obtained residue was subjected to silica gel column chromatography (eluent, ethyl acetate) for purification and recrystallized from ethyl acetate-diisopropyl ether to give the title compound (148 mg) as colorless powder crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionre-dissolved in THF (10 ml)
  5. additionTo this solution was added a solution of azetidine hydrochloride (0.54 g)
  6. dissolutiondissolved in 1N NaOH (10 ml)
  7. extractionThe reaction mixture extracted with ethyl acetate
  8. customthe organic layer was dried
  9. concentrationconcentrated
  10. customThe obtained residue was subjected to silica gel column chromatography (eluent, ethyl acetate) for purification
  11. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-9dde5632b10b482aa106d806fd7cfbd3
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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