Dimethylformamide → HCID 22049686, compound

HRID 1830903Notes

Reaction equation

HRID 1830903 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[C:22]([F:25])([F:24])[F:23])[S:14][CH:15]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.C[N:31](C=O)C>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[C:22]([F:25])([F:24])[F:23])[S:14][CH:15]=2)=[CH:7][C:3]=1[C:4]([NH2:31])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22049750HCID 22049750, compound

Product 1

HCID 22049686HCID 22049686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

2-Fluoro-5-{2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl}benzoic acid (205 mg) was dissolved in THF (5 ml) and thionyl chloride (0.06 ml) and DMF (0.01 ml) were added. The mixture was heated under reflux for 2 hrs. The reaction mixture was concentrated under reduced pressure and re-dissolved in THF (5 ml). 28% Aqueous ammonia (3 ml) cooled to 5° C. was gradually added. The reaction mixture was stirred at room temperature for 30 min. and extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=9:1→ethyl acetate) for purification and recrystallized from ethyl acetate-diisopropyl ether to give the title compound (130 mg) as colorless powder crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionre-dissolved in THF (5 ml)
  5. additionwas gradually added
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was dried
  8. concentrationconcentrated
  9. customThe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=9:1→ethyl acetate) for purification
  10. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-5c2fae585a4842138e5157ea0d0f9e54
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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