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Potassium Fluoride → 4-isopropyl-6-methoxy-2-[1-(2-pyrimidinyl)-3-(trifluoro methyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289853
Notes
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Reaction equation

HRID 1289853 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[C:11]([OH:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]1.[F-].[K+].Br[CH2:20][N:21]1[C:25](=[O:26])[C:24]2[C:27]([CH:33]([CH3:35])[CH3:34])=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:23]=2[S:22]1(=[O:37])=[O:36]>CN(C=O)C.[Cl-].[NH4+]>[CH:33]([C:27]1[C:24]2[C:25](=[O:26])[N:21]([CH2:20][O:12][C:11]3[N:7]([C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)[N:8]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:10]=3)[S:22](=[O:37])(=[O:36])[C:23]=2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=1)([CH3:35])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178516161HCID 178516161, compound

Product 1

HCID 867525504-isopropyl-6-methoxy-2-[1-(2-pyrimidinyl)-3-(trifluoro methyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 60%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 1-(2-pyrimidinyl)-3-trifluoromethyl-5-hydroxypyrazole (314 mg; 1.37 mmol) and KF (132 mg; 2.3 mmol) in 8 ml of DMF was stirred under nitrogen at room temperature and then 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (400 mg, 1.14 mmol) was added. The reaction mixture was stirred at room temperature for 1.25 hours and diluted with cold saturated ammonium chloride solution. The mixture was extracted with ether (3×), the organic layer was dried over magnesium sulfate and then filtered and concentrated in vacuo. The yellow solid residue (495 mg) was dissolved in methylene chloride and was purified by column chromatography (silica gel; 20-40% ethyl acetate/hexane) and recrystallized from ether/hexane to afford 330 mg (60%) of 4-isopropyl-6-methoxy-2-[1-(2-pyrimidinyl)-3-(trifluoro methyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =2-pyrimidinyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 133°-134.5° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1.25 hours
  2. extractionThe mixture was extracted with ether (3×)
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe yellow solid residue (495 mg) was dissolved in methylene chloride
  7. customwas purified by column chromatography (silica gel; 20-40% ethyl acetate/hexane)
  8. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-0a3406668d1945e3b8a9c3d88c9b3dda
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05750550

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes