Cyclopropanecarbonyl chloride → HCID 58247992, compound

HRID 339118Notes

Reaction equation

HRID 339118 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[C:17]([F:20])([F:19])[F:18])=[O:14])=[CH:7][C:6]=1[C:31]([F:34])([F:33])[F:32])[NH2:4].[CH:35]1([C:38](Cl)=O)[CH2:37][CH2:36]1>N1C=CC=CC=1>[CH:35]1([C:38]2[O:1][N:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH:16]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)[C:17]([F:19])([F:20])[F:18])=[O:14])=[CH:7][C:6]=3[C:31]([F:32])([F:33])[F:34])[N:4]=2)[CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86653073HCID 86653073, compound

Product 1

HCID 58247992HCID 58247992, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

80 mg (0.16 mmol) of (2E)-3-[4-(N′-hydroxycarbamimidoyl)-3-(trifluoromethyl)phenyl]-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide from Stage 1 were initially charged in 2 ml of pyridine, admixed at room temperature with 16.7 mg (0.16 mmol) of cyclopropanecarbonyl chloride and heated under reflux for 18 hours. The pyridine was for the most part distilled off under reduced pressure, and the residue was admixed with water and extracted with ethyl acetate. After drying over magnesium sulphate, the solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 0% ethyl acetate to 100% ethyl acetate).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. distillationdistilled off under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialAfter drying over magnesium sulphate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was chromatographed on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 0% ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-07877b1ee81c427a9eb662d61442fa9e
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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