1-Propanesulfonyl chloride → N-(propylsulfonyl)-N-(2,4,5-trifluoro-3-(3-morpholinoquinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide

HRID 929350Notes

Reaction equation

HRID 929350 reaction equation
[NH2:1][C:2]1[C:3]([F:28])=[C:4]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][C:16]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[N:15]3)=[O:11])[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[CH2:29]([S:32](Cl)(=[O:34])=[O:33])[CH2:30][CH3:31]>C(Cl)Cl>[CH2:29]([S:32]([N:1]([C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][C:16]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[N:15]3)=[O:11])[C:3]=1[F:28])[S:32]([CH2:29][CH2:30][CH3:31])(=[O:34])=[O:33])(=[O:34])=[O:33])[CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 86677175(3-Amino-2,5,6-trifluorophenyl)(3-morpholinoquinoxalin-6-yl)methanone

Product 1

HCID 86677176N-(propylsulfonyl)-N-(2,4,5-trifluoro-3-(3-morpholinoquinoxaline-6-carbonyl)phenyl)propane-1-sulfonamideYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,5,6-trifluorophenyl)(3-morpholinoquinoxalin-6-yl)methanone (40 mg, 0.1 mmol, 1.0 eq.) in DCM (10 mL) was added TEA (101 mg, 1 mol, 10 eq.) and propane-1-sulfonyl chloride (0.5 mL, 0.5 mmol, 5.0 eq.). The resulting mixture was stirred at rt for 1 h, then washed with water and extracted with DCM (10 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=2/1, v/v) to afford N-(propylsulfonyl)-N-(2,4,5-trifluoro-3-(3-morpholinoquinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (41 mg, 62.2%).

Workup

  1. washwashed with water
  2. extractionextracted with DCM (10 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (PE/EA=2/1

Sources & evidence

ORD record
ord-0219bf208a634c4bb6204c065685afc5
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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