Mci-186 → HCID 18922581, compound

HRID 1289827Notes

Reaction equation

HRID 1289827 reaction equation
[F-].[K+].[C:3]1([N:9]2[C:13](=[O:14])[CH2:12][C:11]([CH3:15])=[N:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:17][N:18]1[C:22](=[O:23])[C:21]2[C:24]([CH:30]([CH3:32])[CH3:31])=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:20]=2[S:19]1(=[O:34])=[O:33].O.C(OCC)(=O)C>CN(C=O)C>[CH:30]([C:24]1[C:21]2[C:22](=[O:23])[N:18]([CH2:17][O:14][C:13]3[N:9]([C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:10]=[C:11]([CH3:15])[CH:12]=3)[S:19](=[O:34])(=[O:33])[C:20]=2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=1)([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 4021Mci-186HCID 522689Potassium FluorideHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideHCID 22728543Water ethylacetate

Product 1

HCID 18922581HCID 18922581, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 460 mg (7.9 mmol) of KF in DMF (25 ml) was added under nitrogen at room temperature 2,4-dihydro-2-phenyl-5-methyl-3H-pyrazol-3-one (1.38 g; 7.98 mmol) with stirring (5 minutes) followed by 2-chloromethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1.1 g, 3.63 mmol) and the resulting mixture was stirred at room temperature for 6 hours and then poured into water/ethyl acetate. The above mixture was extracted with ethyl acetate (3×75 ml) and the organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue (yellow foam, 1.3 g) was purified by flash chromatography (silica gel; 10-20% ethyl acetate in hexane) to afford 120 mg of 4-isopropyl-6-methoxy-2-(1-phenyl-3-methylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =CH3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white foam, m.p. 65°-670° C.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 6 hours
  2. extractionThe above mixture was extracted with ethyl acetate (3×75 ml)
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue (yellow foam, 1.3 g) was purified by flash chromatography (silica gel; 10-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5b86a3cf98b1454c87b2e5b863f43f8c
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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