Chloroacetone → 2-Cyclopropylamino-4,6-difluoro-benzoic acid 2-oxo-propyl ester

HRID 559062Notes

Reaction equation

HRID 559062 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([NH:10][C:11]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[C:12]=2[C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1.Cl[CH2:23][C:24](=[O:26])[CH3:25]>CN(C=O)C>[O:26]=[C:24]([CH3:25])[CH2:23][O:14][C:13](=[O:15])[C:12]1[C:16]([F:21])=[CH:17][C:18]([F:20])=[CH:19][C:11]=1[NH:10][CH:7]1[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 57687389HCID 57687389, compound

Product 1

HCID 576873912-Cyclopropylamino-4,6-difluoro-benzoic acid 2-oxo-propyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (2.3 g, 16.7 mmol) was added to a solution of example 6a (5.1 g, 23.8 mmol) in DMF (20 mL). The reaction mixture was stirred at 90° C. for 1 h. Chloroacetone (2.21 g, 23.8 mmol) was then added dropwise at room temperature and the reaction mixture was heated at 55° C. for 1.5 h. The reaction mixture was poured into ice. The precipitate was collected by filtration to give 6.53 g (quantitative) of the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.66 (s, 1H), 6.69 (dd, 1H, J=12.0, 1.2 Hz), 6.49 (dt, 1H, J=12.0, 1.2 Hz), 5.02 (s, 2H), 3.34-3.40 (m, 1H), 2.15 (s, 3H), 0.81-0.85 (m, 2H), 0.48-0.52 (m, 2H). MS (ES) [m+H] calc'd for C13H13F2NO3, 269; found 269.

Workup

  1. temperaturethe reaction mixture was heated at 55° C. for 1.5 h
  2. additionThe reaction mixture was poured into ice
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a8aad5a9c96442319974784ce2cad5ce
Source dataset
uspto-grants-2011_11
Patent number
US08063066B2

Reaction notes

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