Potassium Hydroxide → HCID 22281994, compound

HRID 1062788Notes

Reaction equation

HRID 1062788 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([NH2:14])[C:9]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:3])[CH3:2].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].[OH-:36].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([N:14]([S:32]([C:29]2[CH:30]=[CH:31][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=2)(=[O:33])=[O:36])[S:32]([C:29]2[CH:30]=[CH:31][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[C:9]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 22281967HCID 22281967, compound

Product 1

HCID 22281994HCID 22281994, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 2-{[3-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]oxy}ethyl acetate (Preparation 24) (155 mg) in dichloromethane (20 ml) at room temperature was added 4-tert-butylbenzenesulfonyl chloride (374 mg), tetrabutylammonium hydrogen sulfate (45 mg) and potassium hydroxide (374 mg) and then the mixture was sonicated for 5.25 hrs. The reaction was diluted with dichloromethane (100 ml) and washed with water (3×100 ml) and brine (100 ml). The organic fractions were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 10 g) eluted with dichloromethane:hexane (4:1) to yield the title compound as a white solid (38 mg).

Workup

  1. customthe mixture was sonicated for 5.25 hrs
  2. washwashed with water (3×100 ml) and brine (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, 10 g)
  7. washeluted with dichloromethane:hexane (4:1)

Sources & evidence

ORD record
ord-a64133bc36694d39b3706aaab302270f
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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