4-Fluorobenzenesulfonyl chloride → HCID 86730269, compound

HRID 1850215Notes

Reaction equation

HRID 1850215 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH3:18])[N:11]=1)([CH3:3])[CH3:2].[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([N:22]2[CH2:23][CH2:24][CH:19]([C@@H:17]([NH:16][C:12]3[N:11]=[C:10]([N:5]4[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])[CH:15]=[CH:14][N:13]=3)[CH3:18])[CH2:20][CH2:21]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86730270HCID 86730270, compound

Product 1

HCID 86730269HCID 86730269, compoundYield 1.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-4-isopropyl-3-(2-((S)-1-(piperidin-4-yl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one (225 mg, 0.675 mmol), 4-fluorobenzene-1-sulfonyl chloride (146 mg, 0.750 mmol) and DIPEA (1 ml) in CH2Cl2 was stirred at room temperature for 2 h. The reaction mixture was diluted with CH2Cl2 and washed with water. Aqueous layer was extracted with CH2Cl2. Combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give (S)-3-(2-((S)-1-(1-(4-fluorophenylsulfonyl)piperidin-4-yl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (4.5 mg, 0.009 mmol).

Workup

  1. washwashed with water
  2. extractionAqueous layer was extracted with CH2Cl2
  3. washCombined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2ef56c8bc6764f909ef8057b4407cd22
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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