2-(Bromomethyl)-5-(trifluoromethyl)furan → HCID 68662202, compound

HRID 1260858Notes

Reaction equation

HRID 1260858 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Br[CH2:13][C:14]1[O:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1.Cl.CO>CN(C)C=O.C(OCC)(=O)C.CO>[ClH:11].[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2](=[NH:1])[N:10]([CH2:13][C:14]2[O:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)[CH:9]=1

Participants

7

Reactant 3

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 21893726Hydrochloride methanolHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 68662202HCID 68662202, compoundYield 28.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 2-(bromomethyl)-5-(trifluoromethyl)furan (0.30 g), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate. The obtained crystals were dissolved in aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was treated by silica gel chromatography (ethyl acetate 100%→ethyl acetate:methanol=5:1) to give a yellow solid. The obtained solid was dissolved in methanol, and 2N hydrochloric acid-methanol solution (0.3 ml) was added. The solvent was concentrated under reduced pressure and the residue was crystallized from methanol-ethyl acetate to give the title compound (45 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. customThe obtained precipitate was recrystallized from methanol-ethyl acetate
  4. dissolutionThe obtained crystals were dissolved in aqueous sodium hydrogen carbonate solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate 100%→ethyl acetate:methanol=5:1)
  10. customto give a yellow solid
  11. concentrationThe solvent was concentrated under reduced pressure
  12. customthe residue was crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-a65cb74ee2b64af6ad10bc940d1ab503
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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