1-Propanesulfonyl chloride → HCID 117902268, compound

HRID 1771123Notes

Reaction equation

HRID 1771123 reaction equation
[NH2:1][C:2]1[C:3]([F:21])=[C:4]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.[CH2:22]([S:25](Cl)(=[O:27])=[O:26])[CH2:23][CH3:24]>C(Cl)Cl>[F:21][C:3]1[C:4]([C:9]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][CH:15]=[N:14]3)=[O:10])=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[N:1]([S:25]([CH2:22][CH2:23][CH3:24])(=[O:27])=[O:26])[S:25]([CH2:22][CH2:23][CH3:24])(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 89462331HCID 89462331, compound

Product 1

HCID 117902268HCID 117902268, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,6-difluorophenyl)(quinoxalin-6-yl) methanone (50 mg, 0.176 mmol, 1 eq.) in DCM (5 mL) were added TEA (89 mg, 0.88 mmol, 5 eq.) and propane-1-sulfonyl chloride (55 mg, 0.387 mmol, 2.2 eq.). The resulting mixture was stirred at rt for 1 h, then washed with water and extracted with DCM (20 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified via flash column chromatography (PE/EA=2/1, v/v) to afford N-(2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl)-N-(propylsulfonyl)propane-1-sulfonamide (30 mg, 34.5%).

Workup

  1. washwashed with water
  2. extractionextracted with DCM (20 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via flash column chromatography (PE/EA=2/1

Sources & evidence

ORD record
ord-866a103270984dee9fc08c396aeea819
Source dataset
uspto-grants-2016_02
Patent number
US09249110B2

Reaction notes

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