Triethylamine → N-[4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenyl]-4-isopropyl-benzenesulfonamide

HRID 1260260Notes

Reaction equation

HRID 1260260 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22].C(N(CC)CC)C>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:30]([C:27]3[CH:28]=[CH:29][C:24]([CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=3)(=[O:32])=[O:31])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chloride2×HCID 574944484-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenylamine

Product 1

HCID 53628720N-[4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenyl]-4-isopropyl-benzenesulfonamideYield 25.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Benzyl-pyrrolidin-3-yl)-2-fluoro-phenylamine (400 mg, 1.48 mmol) and 4-isopropyl-phenylsulfonyl chloride (324 mg, 1.48 mmol) were dissolved in tetrahydrofuran (25 ml). Triethylamine (0.62 ml, 4.44 mmol) was added and the reaction mixture stirred over night at room temperature (10% conversion) and subsequently refluxed for 4 h (30% conversion). Small portions of 4-isopropyl-phenylsulfonyl chloride and triethylamine were added and the reaction mixture was stirred 15 min at 150° C. in the microwave (CEM). This procedure was repeated until complete conversion was observed. The solvent was evaporated under reduced pressure, the residue treated with ethyl acetate (50 ml) and extracted twice with slightly acidic water. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give an oil (170 mg, 21%).

Workup

  1. temperaturesubsequently refluxed for 4 h (30% conversion)
  2. stirringthe reaction mixture was stirred 15 min at 150° C. in the microwave (CEM)
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue treated with ethyl acetate (50 ml)
  5. extractionextracted twice with slightly acidic water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-26559de8e36844e2af7a79477510aaf2
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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