Water → HCID 12151351, compound

HRID 393146Notes

Reaction equation

HRID 393146 reaction equation
[CH2:1]([C:3]1[C:8]([CH:9]([NH:12][CH3:13])[CH2:10][CH3:11])=[CH:7][N:6]=[CH:5][N:4]=1)[CH3:2].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O.N1C=CC=C[CH:27]=1>>[CH2:1]([C:3]1[C:8]([CH:9]([N:12]([CH3:13])[S:21]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH:10]([CH3:27])[CH3:11])=[CH:7][N:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 22648749HCID 22648749, compound

Product 1

HCID 12151351HCID 12151351, compoundYield 56%

Procedure

0.4 g (0.2 mmol) of [1-(4-ethyl-pyrimidin-5-yl)-propyl]-methyl-amine was dissolved in 20 ml of pyridine, and 0.43 g (0.22 mmol) of p-fluorobenzenesulfonyl chloride was dropwise added, followed by stirring at room temperature for 10 hours. To the reaction solution, 50 ml of water was added, followed by extraction with diethyl ether. The obtained organic phase was washed twice with 30 ml of a dilute citric acid aqueous solution and then dried over anhydrous magnesium sulfate. Diethyl ether was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography (developing solvent/n-hexane:ethyl acetate 4:1 to 1:1) to obtain 0.4 g (yield: 56%) of (N-[1-(4-ethyl-pyrimidin-5-yl)-2-methylpropyl]-4-fluoro-N-methyl-benzenesulfonamide as a colorless oil (nD20=1.5399).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe obtained organic phase was washed twice with 30 ml of a dilute citric acid aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationDiethyl ether was distilled off under reduced pressure
  5. customthe obtained crude product
  6. customwas purified by silica gel chromatography (developing solvent/n-hexane:ethyl acetate 4:1 to 1:1)

Sources & evidence

ORD record
ord-bcbd18eebb264d5196ac8cf8689847cf
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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