Sodium hydride → 5-Chloro-6-((8-fluoro-1,4-dioxaspiro[4.5]decan-8-yl)methoxy)pyridine-3-sulfonamide

HRID 2045101Notes

Reaction equation

HRID 2045101 reaction equation
[F:1][C:2]1([CH2:12][OH:13])[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.[H-].[Na+].[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[N:21][C:22]=1Cl.[NH4+].[Cl-]>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[N:21][C:22]=1[O:13][CH2:12][C:2]1([F:1])[CH2:11][CH2:10][C:5]2([O:6][CH2:7][CH2:8][O:9]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 47309215,6-Dichloropyridine-3-sulfonamideHCID 67225989HCID 67225989, compound

Product 1

HCID 672259855-Chloro-6-((8-fluoro-1,4-dioxaspiro[4.5]decan-8-yl)methoxy)pyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 512B (500 mg) in N,N-dimethylformamide (5 mL) was added NaH (65% in mineral oil, 252 mg) at room temperature. The mixture was stirred for 30 minutes, and then 5,6-dichloropyridine-3-sulfonamide (0.6 g) was added. The mixture was stirred at room temperature overnight. The mixture was poured over aqueous NH4Cl and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water, brine and dried over Na2SO4. After filtration and evaporation of the solvent, the residue was loaded on a silica gel cartridge and eluted with 30% ethyl acetate in hexane to give the pure product.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent
  6. washeluted with 30% ethyl acetate in hexane
  7. customto give the pure product

Sources & evidence

ORD record
ord-f7bfdbe47c594d08b5a0d3a89e998ad0
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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