O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[6-chloro-4-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-pyridin-2-yl]-methanesulphonamide

HRID 74585

Reaktionsgleichung

Reaktionsgleichung von HRID 74585
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[N:10]=1)[C:5]([OH:7])=O.[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH2:21][CH2:20]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[C:4]([C:5]([N:22]2[C:23]3[C:19](=[CH:18][C:17]([F:16])=[CH:25][CH:24]=3)[CH2:20][CH2:21]2)=[O:7])[CH:3]=1

Komponenten

5

Edukt 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-FluoroindolineHCID 866564982-Chloro-6-methanesulphonylamino-isonicotinic acid

Produkt 1

HCID 58386691N-[6-chloro-4-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-pyridin-2-yl]-methanesulphonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.28 g (1.1 mmol) 2-chloro-6-methanesulphonylamino-isonicotinic acid, 0.16 g (1.1 mmol) 5-fluoro-2,3-dihydro-1H-indole, 0.31 mL (2.2 mmol) TEA in 4.0 mL DMF were mixed with 0.39 g (1.2 mmol) TBTU and stirred for 2 h at RT. The reaction mixture was purified by HPLC. The product fractions were combined and evaporated down.

Aufarbeitung

  1. customThe reaction mixture was purified by HPLC
  2. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-e79c9f683b0c4d6392fa55d1e6acb89d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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