Pyridine → HCID 131734351, compound

HRID 1505487Notes

Reaction equation

HRID 1505487 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([NH2:15])[C:9]=1[F:16])([CH3:4])([CH3:3])[CH3:2].[CH3:18][CH:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20].N1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([NH:15][S:21]([CH:19]([CH3:20])[CH3:18])(=[O:23])=[O:22])[C:9]=1[F:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 824082-Propanesulfonyl chlorideHCID 70700579tert-Butyl (3-amino-2,6-difluorophenyl)carbamate

Product 1

HCID 131734351HCID 131734351, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

The tert-butyl-3-amino-2,6-difluorophenylcarbamate (100 mg, 0.41 mmol) prepared at Step 3 was added and dissolved into dichloromethane solvent. 2-propane sulfonyl chloride (50 uL, 0.45 mmol) and pyridine (36 uL, 0.045 mmol) were added into the reaction solution and stirred at 50° C. for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 94 mg of the target compound, tert-butyl-2,6-difluoro-3-(1-methylethylsulfonamido)phenylcarbamate (percentage yield: 65%), was obtained.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. washthe reactant was washed with 1N aqueous hydrochloric acid solution and salt water
  4. extractionAfter extraction with dichloromethane
  5. dry with materialthe organic layer was dried with sulfuric anhydride magnesium and vacuum
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b0696f16d7f04a6daf998458f87585f0
Source dataset
uspto-grants-2015_12
Patent number
US09216981B2

Reaction notes

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