1-Propanesulfonyl chloride → HCID 86677181, Verbindung

HRID 929356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929356
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

Komponenten

4

Edukt 2

HCID 662791-Propanesulfonyl chlorideHCID 86677182HCID 86677182, Verbindung

Produkt 1

HCID 86677181HCID 86677181, VerbindungAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a3bb13f36f51410d923c5ace09f2bffc
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09295671B2

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