Ethyl Acetate → HCID 68662288, compound

HRID 1260879Notes

Reaction equation

HRID 1260879 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[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[F:22].C(OCC)(=O)C>CN(C=O)C>[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[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[F:22])[CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27831494-(Bromomethyl)-3-fluorobenzonitrileHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 68662288HCID 68662288, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-5-chloronicotinamide (150 mg) and 4-(bromomethyl)-3-fluorobenzonitrile (282 mg) in DMF (3 ml) was stirred at 100° C. for 24 hr. After cooling to room temperature, ethyl acetate was added, and the precipitated crystals were filtered. The obtained crystals were dissolved in methanol (3 ml) and partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organic layer was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0-9/1). 4N Hydrochloric acid-ethyl acetate solution was added to the obtained yellow oil, and the precipitated crystals were filtered and recrystallized to give the title compound (47 mg).

Workup

  1. filtrationthe precipitated crystals were filtered
  2. dissolutionThe obtained crystals were dissolved in methanol (3 ml)
  3. custompartitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0-9/1)
  8. addition4N Hydrochloric acid-ethyl acetate solution was added to the obtained yellow oil
  9. filtrationthe precipitated crystals were filtered
  10. customrecrystallized

Sources & evidence

ORD record
ord-2a3b0cb196204875991d638c774040b1
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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