1-Propanesulfonyl chloride → HCID 86677181, compound

HRID 929356Notes

Reaction equation

HRID 929356 reaction equation
Cl.[NH2:2][C:3]1[C:4]([F:30])=[C:5]([C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][C:17]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[N:16]3)=[O:12])[C:6]([F:10])=[C:7]([F:9])[CH:8]=1.[CH2:31]([S:34](Cl)(=[O:36])=[O:35])[CH2:32][CH3:33]>C(Cl)Cl>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:17]2[CH:18]=[N:19][C:20]3[C:15]([N:16]=2)=[CH:14][C:13]([C:11]([C:5]2[C:4]([F:30])=[C:3]([N:2]([S:34]([CH2:31][CH2:32][CH3:33])(=[O:36])=[O:35])[S:34]([CH2:31][CH2:32][CH3:33])(=[O:36])=[O:35])[CH:8]=[C:7]([F:9])[C:6]=2[F:10])=[O:12])=[CH:22][CH:21]=3)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 86677182HCID 86677182, compound

Product 1

HCID 86677181HCID 86677181, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,5,6-trifluorophenyl)(3-(4-chlorophenyl)quinoxalin-6-yl)methanone hydrochloride (100 mg, 0.24 mmol, 1.0 eq.) in DCM (10 mL) were added TEA (242 mg, 2.4 mmol, 10.0 eq.) and propane-1-sulfonyl chloride (172 mg, 1.2 mmol, 5.0 eq.). The resulting mixture was stirred at rt for 1 h, then concentrated. The resulting residue was dissolved in EA (10 mL) and washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=4/1, v/v) to afford N-(3-(3-(4-chlorophenyl)quinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)-N- (propylsulfonyl)propane-1-sulfonamide (50 mg, 40.3%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in EA (10 mL)
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash column chromatography (PE/EA=4/1

Sources & evidence

ORD record
ord-a3bb13f36f51410d923c5ace09f2bffc
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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