2-Chloro-5-methanesulfonylpyrimidine → N-[4-(1,3-benzodioxol-5-yl)-1-methyl-3-(2-{[5-(methylsulfonyl)-2-pyrimidinyl]oxy}ethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

HRID 1368610Notes

Reaction equation

HRID 1368610 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:30][CH2:31][CH2:32][OH:33])=[N:12][N:13]([CH3:29])[C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl[C:35]1[N:40]=[CH:39][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[CH:37][N:36]=1>O1CCCC1.CC(N(C)C)=O.[H-].[Na+]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:30][CH2:31][CH2:32][O:33][C:35]4[N:40]=[CH:39][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[CH:37][N:36]=4)=[N:12][N:13]([CH3:29])[C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 2

HCID 156534822-Chloro-5-methanesulfonylpyrimidineHCID 22282036N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

Product 1

HCID 9809402N-[4-(1,3-benzodioxol-5-yl)-1-methyl-3-(2-{[5-(methylsulfonyl)-2-pyrimidinyl]oxy}ethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamideYield 16.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 17) (300 mg, 0.63 mmol) in anhydrous tetrahydrofuran (12 ml) and dimethyl acetamide, sodium hydride 60% dispersion in oil (55 mg, 1.39 mmol) was added under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 20 minutes. 2-chloro-5-(methylsulfonyl)pyrimidine (0.69 mmol) was added, in one portion, to the reaction mixture which was then stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue poured onto water (150 ml). The aqueous was extracted with ethyl acetate (4×50 ml). The organic fractions were washed with brine (4×100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to yield the title compound (65 mg) as a yellow crystalline solid.

Workup

  1. stirringwas then stirred at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue poured onto water (150 ml)
  4. extractionThe aqueous was extracted with ethyl acetate (4×50 ml)
  5. washThe organic fractions were washed with brine (4×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2737875c29ba41378e5be65d2b09292a
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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