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 → 4-chloro-N-[5-chloro-2-(3,4-dihydro-2H-benzo[1,4]oxazine-8-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 419165Notes

Reaction equation

HRID 419165 reaction equation
C(OC([N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([C:20]3[C:25]([N:26]([S:30]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([C:40]([F:43])([F:42])[F:41])[CH:34]=4)(=[O:32])=[O:31])COC)=[CH:24][C:23]([Cl:44])=[CH:22][N:21]=3)=[O:19])[C:12]=2[O:11][CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([S:30]([NH:26][C:25]2[C:20]([C:18]([C:17]3[C:12]4[O:11][CH2:10][CH2:9][NH:8][C:13]=4[CH:14]=[CH:15][CH:16]=3)=[O:19])=[N:21][CH:22]=[C:23]([Cl:44])[CH:24]=2)(=[O:31])=[O:32])=[CH:34][C:35]=1[C:40]([F:42])([F:43])[F:41]

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 582681504-chloro-N-[5-chloro-2-(3,4-dihydro-2H-benzo[1,4]oxazine-8-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamideYield 52.4%

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° C. 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-N-[5-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-6f2ad7d2b14c469db05a3bcec2dd6053
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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