1-Propanesulfonyl chloride → HCID 86677170, compound

HRID 929341Notes

Reaction equation

HRID 929341 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[C:4]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[N:15]3)=[O:11])[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[CH2:23]([S:26](Cl)(=[O:28])=[O:27])[CH2:24][CH3:25]>C(Cl)Cl>[CH2:23]([S:26]([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][CH:16]=[N:15]3)=[O:11])[C:3]=1[F:22])[S:26]([CH2:23][CH2:24][CH3:25])(=[O:28])=[O:27])(=[O:28])=[O:27])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 86677171HCID 86677171, compound

Product 1

HCID 86677170HCID 86677170, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,5,6-trifluorophenyl)(quinoxalin-6-yl)methanone (300 mg, 1 mmol, 1 eq.) in DCM (30 mL) was added TEA (1.0 g mg, 10 mmol, 10 eq.), followed by propane-1-sulfonyl chloride (713 mg, 5 mmol, 5 eq.). After the resulting mixture was stirred at rt for 1 h, the mixture was washed with water and extracted with DCM (20 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-(quinoxaline-6-carbonyl)phenyl)propane-1-sulfonamide (170 mg, 33.0%).

Workup

  1. washthe mixture was washed with water
  2. extractionextracted with DCM (20 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-eb49292fb6dc4d40a9d03bf51b2eb33d
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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