Dimethylformamide → HCID 14146225, compound

HRID 1396120Notes

Reaction equation

HRID 1396120 reaction equation
[OH:1][CH2:2][C:3]1([NH:6][CH:7]=[C:8]([C:14](=[O:25])[C:15]2[CH:20]=[C:19](F)[C:18]([F:22])=[C:17]([F:23])[C:16]=2F)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(OC(=O)C)C>[F:23][C:17]1[CH:16]=[C:15]2[C:20]3=[C:19]([O:1][CH2:2][C:3]4([CH2:5][CH2:4]4)[N:6]3[CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]2=[O:25])[C:18]=1[F:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 178471963HCID 178471963, compound

Product 1

HCID 14146225HCID 14146225, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of ethyl 3-(1-(hydroxymethyl)cyclopropylamino)-2-(2,3,4,5-tetrafluoro-benzoyl)acrylate (300 mg, 0.83 mmol), K2CO3 powder (344 mg, 2.49 mmol), and 3 ml of anhydrous DMF were heated in a CEM Discover microwave for 10 min at 200° C. After that the sample was rapidly cooled to room temperature yielding a dark brown liquid. The DMF was removed by evaporation to give a dark solid. The solid was dissolved in 50 ml of ethylacetate and washed two times with 10 ml of water. The organic layer was dried over Na2SO4 to afford a light yellow solid as the title compound which was used without further purification in the next step (133 mg, 0.415 mmol). MS (EP) m/z: 322 (M++1). (Calcd. for C16H13F2NO4, 321.28)

Workup

  1. temperatureAfter that the sample was rapidly cooled to room temperature
  2. customyielding a dark brown liquid
  3. customThe DMF was removed by evaporation
  4. customto give a dark solid
  5. washwashed two times with 10 ml of water
  6. dry with materialThe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-f7eb6f2281a74f2f891a5eed9f32ddc0
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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