3-Chloro-4-(3-fluorobenzyloxy)aniline → HCID 57597156, compound

HRID 1925984Notes

Reaction equation

HRID 1925984 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH3:11])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[NH2:16]>CN1CCCC1=O.C(=O)([O-])O.[Na+]>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[C:3]3[N:10]([CH3:11])[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1

Participants

5

Reactant 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 594245054-Chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 57597156HCID 57597156, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (100 mg) in 1-methyl-2-pyrrolidone (1.0 mL) was added 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (225 mg), and the mixture was heated to 140° C. and stirred for 1.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carbonate solution (25 mL), and extracted with ethyl acetate (30 mL×3). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (eluent:hexane/ethyl acetate=95/5→0/100). The object fraction was concentrated under reduced pressure. The residue was recrystallized from a mixed solvent of diisopropyl ether and chloroform, collected by filtration and dried under reduced pressure to give the title compound (121 mg) as a pale-purple powder crystals.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (30 mL×3)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of diisopropyl ether and chloroform
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-9da0dda9afd44e8bba38eb3c90f8dd94
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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