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Water → N-[3-{2-[(5-chloropyrimidin-2-yl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]pyridine-2-sulphonamide

HRID 1368600
Notes
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Reaction equation

HRID 1368600 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[C:8]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)(=[O:20])=[O:19])[N:7]([CH3:27])[N:6]=1.[H-].[Na+].[Cl:30][C:31]1[CH:32]=[N:33][C:34](S(C)(=O)=O)=[N:35][CH:36]=1.O>O1CCCC1>[Cl:30][C:31]1[CH:32]=[N:33][C:34]([O:1][CH2:2][CH2:3][O:4][C:5]2[C:9]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[C:8]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)(=[O:19])=[O:20])[N:7]([CH3:27])[N:6]=2)=[N:35][CH:36]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27277255-Chloro-2-methanesulfonylpyrimidineHCID 22281891N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-pyridine-2-sulphonamide

Product 1

HCID 22281915N-[3-{2-[(5-chloropyrimidin-2-yl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]pyridine-2-sulphonamide
Yield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-2-pyridine sulphonamide (Example 52) (200 mg) in dry tetrahydrofuran (2 ml) at room temperature was added sodium hydride (80% dispersion in oil, 35 mg) the mixture was stirred for 10 minutes. A solution of 5-chloro-2-methylsulphonylpyrimidine (134 mg) in dry tetrahydrofuran (2.5 ml) was then added and the mixture was stirred for a further 4 hours. The mixture was stirred for 4 hours. The reaction was treated with water (50 ml) and extracted with ethyl acetate (50 ml). The aqueous phase was neutralised to pH7 with 2N hydrochloric acid (aq.). The organic fraction was washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with a solvent gradient of pentane:ethyl acetate (1:1 to 0:1) to yield the tile compound as a colourless foam (120 mg).

Workup

  1. stirringthe mixture was stirred for a further 4 hours
  2. stirringThe mixture was stirred for 4 hours
  3. extractionextracted with ethyl acetate (50 ml)
  4. washThe organic fraction was washed with brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica (10 g)
  9. washeluted with a solvent gradient of pentane:ethyl acetate (1:1 to 0:1)

Sources & evidence

ORD record
ord-2bc56184618d48a8974c1a9ae848b02d
Source dataset
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06573270B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes