Dimethylformamide → HCID 67641417, compound

HRID 1289864Notes

Reaction equation

HRID 1289864 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][C:9]([C:13]3C=CC=CC=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.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].[F-].[K+].C[N:41](C=O)C>>[CH:33]([C:27]1[C:24]2[C:25](=[O:26])[N:21]([CH2:20][O:12][C:11]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]([C:13]#[N:41])[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]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 785593H-Pyrazol-3-one, 2,4-dihydro-2,5-diphenyl-2×HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 67641417HCID 67641417, compoundYield 47%

Procedure

A mixture of 2,4-dihydro-2--phenyl-5-cyano-3H-pyrazol-3-one (Formula III: R1 =Ph; R2 =CN; R3 =H) (366 mg; 1.98 mmol), 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (689 mg, 1.98 mmol), and KF (230 mg, 3.91 mmol) in 8 ml of DMF was stirred at room temperature for 3 hours and the resulting mixture was diluted with ice/water. The solid product was filtered, the residual solid was redissolved in ether/water, and the aqueous layer was extracted with ether (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo, and the residue was purified by column chromatography (silica gel; 12-50% ethyl acetate in hexane) and recrystallized from ethyl acetate/hexane to afford 420 mg (47%) of 4-isopropyl-6-methoxy-2-(1-phenyl-3-cyanopyrazol-5-yl-oxymethyl)-1,2-benziso thiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =CN; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 114°-116° C.

Workup

  1. filtrationThe solid product was filtered
  2. dissolutionthe residual solid was redissolved in ether/water
  3. extractionthe aqueous layer was extracted with ether (3×)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (silica gel; 12-50% ethyl acetate in hexane)
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-943ddbcddb3544399c529d588b67d20e
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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