Sodium hydride → 5-Chloro-6-((2-oxo-1-oxa-3-azaspiro[4.5]decan-8-yl)methoxy)pyridine-3-sulfonamide

HRID 574975Notes

Reaction equation

HRID 574975 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:13][CH2:12][C:6]2([O:10][C:9](=[O:11])[NH:8][CH2:7]2)[CH2:5][CH2:4]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>O1CCCC1.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:1][CH2:2][CH:3]1[CH2:13][CH2:12][C:6]2([O:10][C:9](=[O:11])[NH:8][CH2:7]2)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 47309215,6-Dichloropyridine-3-sulfonamideHCID 575765318-(Hydroxymethyl)-1-oxa-3-azaspiro[4.5]decan-2-one

Product 1

HCID 671266985-Chloro-6-((2-oxo-1-oxa-3-azaspiro[4.5]decan-8-yl)methoxy)pyridine-3-sulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 385C (325 mg, 1.755 mmol) in a mixture of tetrahydrofuran (16 mL) and N,N-dimethylformamide (8 mL) was added sodium hydride (281 mg, 7.02 mmol) and the mixture was stirred for 30 minutes. 5,6-Dichloropyridine-3-sulfonamide (389 mg) was added and the reaction was stirred for 42 hours. The reaction was quenched with water (5 mL) and concentrated. The residue was diluted with 75% brine (200 mL) and extracted with methylene chloride (3×200 mL). The organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel and eluted with a 1, 5, and 10% methanol in methylene chloride step gradient to provide the title compound.

Workup

  1. stirringthe reaction was stirred for 42 hours
  2. customThe reaction was quenched with water (5 mL)
  3. concentrationconcentrated
  4. additionThe residue was diluted with 75% brine (200 mL)
  5. extractionextracted with methylene chloride (3×200 mL)
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel
  10. washeluted with a 1, 5, and 10% methanol in methylene chloride step gradient

Sources & evidence

ORD record
ord-af37d3b9bacf41fb93960001a1ffa98c
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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