Triethylamine → N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)pyridine-3-sulfonamide

HRID 572209

Reaktionsgleichung

Reaktionsgleichung von HRID 572209
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C@@H:19]([NH:21][C:22]2[CH:27]=[N:26][CH:25]=[C:24]([Cl:28])[N:23]=2)[CH3:20])[CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Cl:28][C:24]1[N:23]=[C:22]([NH:21][C@H:19]([C:15]2[CH:14]=[C:13]([NH:12][S:8]([C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)(=[O:10])=[O:9])[CH:18]=[CH:17][CH:16]=2)[CH3:20])[CH:27]=[N:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 25218447(S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine

Produkt 1

HCID 25218450N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)pyridine-3-sulfonamideAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of pyridine-3-sulfonylchloride hydrochloride (94 mg, 0.44 mmol) and N-[(1S)-1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (100 mg, 0.4 mmol) in dichloromethane (5 mL) was added triethylamine (0.17 mL, 1.2 mmol) dropwise at room temperature and the mixture was stirred for 17 hours. After this time the mixture was diluted with ethyl acetate (20 mL), washed successively with saturated aqueous sodium hydrogen carbonate (2×20 mL) and brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give a yellow oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)pyridine-3-sulfonamide (44 mg, 28%) as a pale yellow foam.

Aufarbeitung

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate (2×20 mL) and brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow oil which
  5. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7a9cede1e5ee4d758212fa9731856dc6
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029386B2

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