Water → HCID 22339517, compound

HRID 585133Notes

Reaction equation

HRID 585133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]2)[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([NH2:17])[CH:10]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.O>N1C=CC=CC=1>[Cl:18][C:6]1[CH:5]=[C:4]([N:19]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[CH:21]=[N:20]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([NH:17][S:34]([C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 95884-Fluorobenzenesulfonyl chlorideHCID 22339553HCID 22339553, compound

Product 1

HCID 22339517HCID 22339517, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2-[3,5-dichloro-4-(3-amino-4-methoxy-phenoxy)-phenyl]-2H-[1,2,4]triazine-3,5-dione (100 mg) in pyridine (1 mL) was added 4-fluorobenzenesulfonyl chloride (59 mg) and the resulting solution was allowed to stir at room temperature for 1 h. The reaction solution was poured over water, extracted with ethyl acetate, the organic layer washed with 1N hydrochloric acid, water, brine, dried (Na2SO4), concentrated in vacuo and flash chromatographed on silica gel (40% acetone/hexanes) to afford the title compound of Step B as a light-yellow colored solid, 115 mg. m.p. 90-96° C., MS Calc.:553.4; Found:550.9.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer washed with 1N hydrochloric acid, water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo and flash
  5. customchromatographed on silica gel (40% acetone/hexanes)

Sources & evidence

ORD record
ord-946726b565ef46ff9f9d7ba07468c41e
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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