Ethyl Acetate → 2-[(5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy]ethyl acetate

HRID 1062786Notes

Reaction equation

HRID 1062786 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:13])=[C:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:10]([CH3:28])[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:31][O:32][CH2:33][CH2:34][O:35][CH2:36]Cl.C(OCC)(=O)C>O1CCCC1.[Cl-].[NH4+]>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:13])=[C:11]([N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[N:10]([CH3:28])[N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 222820342-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

Product 1

HCID 222818952-[(5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy]ethyl acetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-1-methyl-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 7) (8 g) in solution in tetrahydrofuran (200 ml) was added sodium hydride (860 mg of a 60% dispersion in oil), at room temperature. The reaction was stirred at room temperature for 0.5 hours and 2-methoxyethoxymethyl chloride (2.7 ml) was added dropwise. The reaction was stirred for an other 0.5 hours and was then diluted with a saturated aqueous solution of ammonium chloride (50 ml) and reduced under reduced pressure. Ethyl acetate (100 ml) was added and the organic layer separated. The organics were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was to purified by chromatography on a suction column packed with silica eluted with ethyl acetate hexane (1:1) to yield the desired product as pale yellow oil (9.5 g).

Workup

  1. stirringThe reaction was stirred for an other 0.5 hours
  2. customthe organic layer separated
  3. washThe organics were washed with brine (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto purified by chromatography on a suction column
  8. washeluted with ethyl acetate hexane (1:1)

Sources & evidence

ORD record
ord-644e88e5348842b3940921233f4842e5
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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