8-{5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid tert-butyl ester → 3-(Trifluoromethyl)benzene-1-sulfonamide

HRID 1438606

Reaktionsgleichung

Reaktionsgleichung von HRID 1438606
C(OC(N1C2C=CC=C(C(C3C([N:26]([S:30]([C:33]4[CH:38]=[CH:37][C:36](Cl)=[C:35]([C:40]([F:43])([F:42])[F:41])[CH:34]=4)(=[O:32])=[O:31])COC)=CC(Cl)=CN=3)=O)C=2OCC1)=O)(C)(C)C>Cl.O>[F:43][C:40]([F:41])([F:42])[C:35]1[CH:34]=[C:33]([S:30]([NH2:26])(=[O:32])=[O:31])[CH:38]=[CH:37][CH:36]=1

Komponenten

4

Edukt 1

HCID 666490618-{5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid tert-butyl ester

Produkt 1

HCID 2440763-(Trifluoromethyl)benzene-1-sulfonamideAusbeute 123,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 8-{5-chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-2,3-dihydro-benzo [1,4]oxazine-4-carboxylic acid tert-butyl ester (510.2 mg) in 3 mL HCl (4 M in dioxane) and water (1 mL) was heated at 80 OC for overnight. Upon cooling to room temperature, the mixture was concentrated and the residue was purified by flash column chromatography on silica gel to afford 4-chloro-NJ5-chloro-2-(3,4-dihydro-2H-benzo[1,4]oxazine-8-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (210.2 mg) as white solid. MS m/z: 531.9 (M+H)+.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-fb07e624f6e54ff9ac3d17df4ee4ab20
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622583B2

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