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 1438606Notes

Reaction equation

HRID 1438606 reaction equation
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

Participants

4

Reactant 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

Product 1

HCID 2440763-(Trifluoromethyl)benzene-1-sulfonamideYield 123.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-fb07e624f6e54ff9ac3d17df4ee4ab20
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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