Pyrazole → HCID 54246946, compound

HRID 343874Notes

Reaction equation

HRID 343874 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:14]2[C:9](=[C:10]([F:26])[CH:11]=[C:12]([C:16]([C:18]3[CH:19]=[N:20][N:21]([CH2:24][CH3:25])[C:22]=3[OH:23])=[O:17])[C:13]=2[Cl:15])[S:8](=[O:28])(=[O:27])[CH2:7][CH2:6]1.N1C=CC=N1.C(=O)([O-])[O-].[K+].[K+].[CH2:40]([S:43](Cl)(=[O:45])=[O:44])[CH2:41][CH3:42]>ClCCl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:1][CH2:2][CH2:3][O:4][CH:5]1[C:14]2[C:9](=[C:10]([F:26])[CH:11]=[C:12]([C:16]([C:18]3[CH:19]=[N:20][N:21]([CH2:24][CH3:25])[C:22]=3[O:23][S:43]([CH2:40][CH2:41][CH3:42])(=[O:45])=[O:44])=[O:17])[C:13]=2[Cl:15])[S:8](=[O:27])(=[O:28])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178463136HCID 178463136, compound

Product 1

HCID 54246946HCID 54246946, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

0.69 Gram (1.6 mmol) of the 4-(2-fluoroethoxy)-5-chloro-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonyl-8-fluorothiochroman-1,1-dioxide (corresponding to pyrazole derivative of the formula (Ia)) obtained in Preparation Example 9 was dissolved in 5 ml of dichloromethane, and a solution of 0.26 g (1.9 mmol) of potassium carbonate as a base in 2 ml of water was added. To this mixture was added 0.21 ml (1.9 mmol) of n-propanesulfonyl chloride (corresponding to compound of the formula (IV)) as a reaction reagent, and 0.05 g (0.2 mmol) of benzyltriethylammonium chloride as a phase transfer catalyst was added. The mixture was allowed to react at room temperature for 1 day. After the completion of the reaction, water and dichloromethane were added to separate the reaction mixture to two phases. The resultant organic layer was consecutively washed with distilled water, with a saturated sodium hydrogencarbonate and with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel; hexane:ethyl acetate=1:1) to give 0.52 g (yield 60%) of the subject end product.

Workup

  1. additionwas added
  2. customto react at room temperature for 1 day
  3. additionwere added
  4. customto separate the reaction mixture to two phases
  5. washThe resultant organic layer was consecutively washed with distilled water, with a saturated sodium hydrogencarbonate and with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by column chromatography (silica gel; hexane:ethyl acetate=1:1)
  9. customto give 0.52 g (yield 60%) of the subject end product

Sources & evidence

ORD record
ord-56fd07cefcf24be2a039c1d15dd1baf4
Source dataset
uspto-grants-1999_01
Patent number
US05863866

Reaction notes

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