Sodium hydride → N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-N-(methoxymethyl)-2-phenyl-1-ethanesulfonamide

HRID 1368664Notes

Reaction equation

HRID 1368664 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:29][CH3:30])=[N:14][NH:15][C:16]=3[NH:17][S:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1.[CH3:31][O:32][CH2:33]Br.[Cl-].[NH4+]>O1CCCC1>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:29][CH3:30])=[N:14][NH:15][C:16]=3[N:17]([CH2:31][O:32][CH3:33])[S:18]([CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 83093Bromomethyl methyl etherHCID 22281999N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamide

Product 1

HCID 22282022N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-N-(methoxymethyl)-2-phenyl-1-ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 5 mg) was added at room temperature under an atmosphere of nitrogen to a solution of N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamide (Preparation 56) in anhydrous tetrahydrofuran (2.5 ml). After 10 minutes, bromomethyl methyl ether (12 μl) was added and the reaction was stirred overnight. An aqueous saturated solution of ammonium chloride (4 ml) was added and the mixture was extracted with ethyl acetate (3×6 ml). The combined organic fractions were washed with brine (6 ml), dried over sodium sulfate and concentrated under reduced pressure. The oily residue was purified by column chromatography (Sep-Pak)™ eluted with hexane:ethyl acetate (4:1) then with hexane:ethyl acetate (1:1) to yield the title compound as a white solid (40 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×6 ml)
  2. washThe combined organic fractions were washed with brine (6 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe oily residue was purified by column chromatography (Sep-Pak)™
  6. washeluted with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-a9a9b29ca381415a9daa3341d9cd1f8d
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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