Pyridine → HCID 6468856, compound

HRID 1187298Notes

Reaction equation

HRID 1187298 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])C1C=CC=CC=1.N1C=CC=CC=1.[CH2:26]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[CH3:27]>ClCCl.CN(C1C=CC=CN=1)C>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[NH:10][S:34]([C:31]1[CH:32]=[CH:33][C:28]([CH2:26][CH3:27])=[CH:29][CH:30]=1)(=[O:36])=[O:35]

Participants

6

Reactant 3

HCID 1049PyridineHCID 5709594-Ethylbenzene-1-sulfonyl chlorideHCID 11954520Benzyl (2,4-difluorophenyl)carbamate

Product 1

HCID 6468856HCID 6468856, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2,4-difluoro-phenylamine (30, 2.0 g, 15.5 mmol) in 20 mL of dichloromethane, pyridine (1.326 mL, 16.4 mmol) and dimethylaminopyridine (0.076 g, 0.62 mmol) are added followed by the dropwise addition of 4-ethyl-benzenesulfonyl chloride (59, 3.357 g, 16.4 mmol) and the reaction is heated to reflux overnight. The reaction is concentrated under vacuum to dryness, then brought up in ethyl acetate and water for extraction. The organic layer is isolated and concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with a gradient of 10-20% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (60, 4.344 g).

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction is concentrated under vacuum to dryness
  4. extractionwater for extraction
  5. customThe organic layer is isolated
  6. concentrationconcentrated under vacuum
  7. customThe resulting material is purified by silica gel column chromatography
  8. washeluting with a gradient of 10-20% ethyl acetate in hexane
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1f6d5ae2c18e4ab88317503849595135
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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