Dimethylformamide → HCID 86752549, compound

HRID 1289839Notes

Reaction equation

HRID 1289839 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([OH:13])=[CH:11][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Br[CH2:32][N:33]1[C:37](=[O:38])[C:36]2[C:39]([CH:45]([CH3:47])[CH3:46])=[CH:40][C:41]([O:43][CH3:44])=[CH:42][C:35]=2[S:34]1(=[O:49])=[O:48]>CO.O>[CH:45]([C:39]1[C:36]2[C:37](=[O:38])[N:33]([CH2:32][O:13][C:12]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[N:9]=[C:10]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[CH:11]=3)[S:34](=[O:49])(=[O:48])[C:35]=2[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=1)([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178515684HCID 178515684, compound

Product 1

HCID 86752549HCID 86752549, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(4-chlorophenyl)-3-(4-pyridyl)-5-hydroxy pyrazole (406 mg; 1.49 mmol) and Cs2CO3 (243 mg; 0.75 mmol) in methanol (8 ml) was stirred at room temperature for 4 hours. The solvent was concentrated in vacuo, and the residue was dried in vacuo overnight. To the above residue was added 7 ml of DMF and 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (519 mg, 1.49 mmol) and the resulting mixture was stirred at room temperature for 5 hours and poured into water. The above mixture was extracted with methylene chloride (3×), the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica gel; 33-50% ethyl acetate/hexane; 12-50% methylene chloride/acetone) and recrystallized from methylene chloride/hexane to afford 401 mg (50%) of 4-isopropyl-6-methoxy-2-[1-(4-chlorophenyl)-3-(4-pyridyl) pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =4-Cl--Ph; R2 =4-pyridyl; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. >190° C. (dec.).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was dried in vacuo overnight
  3. stirringthe resulting mixture was stirred at room temperature for 5 hours
  4. extractionThe above mixture was extracted with methylene chloride (3×)
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel; 33-50% ethyl acetate/hexane; 12-50% methylene chloride/acetone)
  8. customrecrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-7b4412d9ffd14dca92f3489eda72ace1
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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