Diisopropylethylamine → N-[3-(3,5-Dimethoxy-phenylamino)-quinoxalin-2-yl]-3-methanesulfonyl-benzenesulfonamide

HRID 336809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336809
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]([NH:22][S:23]([C:26]3[CH:27]=[C:28](NC(C4CNC4)=O)[CH:29]=[CH:30][CH:31]=3)(=[O:25])=[O:24])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CCN(C(C)C)C(C)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:27]=3)(=[O:24])=[O:25])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Komponenten

4

Edukt 2

HCID 81531DiisopropylethylamineHCID 57448472N-(3-(N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)azetidine-3-carboxamide

Produkt 1

HCID 16045082N-[3-(3,5-Dimethoxy-phenylamino)-quinoxalin-2-yl]-3-methanesulfonyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

N-(3-(N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)-sulfamoyl)phenyl)azetidine-3-carboxamide (125 mg, 0.23 mmol), prepared using procedures similar to those described in Example 372, was dissolved into 5 mL DCE in a mL round-bottom flask. DIEA (1.17 mmol, 5.0 equiv.) was then added with stirring followed by acid chloride (0.47 mmol, 2.0 equiv.). The reaction was then stirred at room temperature for 1 hour or until complete as indicated by LCMS. The solvent was subsequently removed under reduced pressure on a rotary evaporator. The crude material was then redissolved in methanol. Purification of the final product was accomplished by preparatory reverse-phase HPLC with the eluents 25 mM aqueous NH4OAc/CAN. A Waters Fractionlynx preparative reverse-phase HPLC; equipped with a Waters SunFire Prep C18, OCD 5 μM, 30×70 mm column and running a 5-100% gradient with a binary solvent system of 25 mM ammonium acetate in water/acetonitrile; was used to carry out the purification.

Aufarbeitung

  1. stirringThe reaction was then stirred at room temperature for 1 hour
  2. customThe solvent was subsequently removed under reduced pressure on a rotary evaporator
  3. dissolutionThe crude material was then redissolved in methanol
  4. customPurification of the final product
  5. customequipped with a Waters SunFire Prep C18, OCD 5 μM, 30×70 mm column
  6. customthe purification

Quellen und Nachweise

ORD-Eintrag
ord-6f03b5ffbc1645f6b15fdb9bcdb64591
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889664B2

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