2,4-Difluoroaniline → HCID 17954364, compound

HRID 1350094Notes

Reaction equation

HRID 1350094 reaction equation
[CH2:1]([NH:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25]>CN(C=O)C.CCOC(C)=O>[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH:25][C:24]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=1[F:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97092,4-DifluoroanilineHCID 81531Diisopropylethylamine2×HCID 96233N-Benzyl-2-chloroacetamide2×

Product 1

HCID 17954364HCID 17954364, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-benzyl-2-chloroacetamide (700 mg—obtained as described for intermediate 1), DIPEA (0.76 mL) and 2,4-difluoro-aniline (0.4 mL) in anhydrous DMF (5 mL) was stirred at 100° C. for 40 hours under a Nitrogen atmosphere. Then, more DIPEA (0.2 mL) was added and the mixture was heated to 100° C. for further 4 hours. After cooling to room temperature, the solution was diluted with AcOEt and washed with water and ice. The separated aqueous phase was extracted with further AcOEt (3×20 mL). The combined organic extracts were dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt 7:3) to give the title compound (600 mg) as a beige solid.

Workup

  1. temperaturethe mixture was heated to 100° C. for further 4 hours
  2. temperatureAfter cooling to room temperature
  3. washwashed with water and ice
  4. extractionThe separated aqueous phase was extracted with further AcOEt (3×20 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (CH/AcOEt 7:3)

Sources & evidence

ORD record
ord-f244d97d7b12416f95d805c3d542f455
Source dataset
uspto-grants-2007_05
Patent number
US07214680B2

Reaction notes

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