Sodium Methoxide → 2-(4-methoxycarbonylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 1384226Notes

Reaction equation

HRID 1384226 reaction equation
C(OC([N:8]([C:28]1[C:33]([O:34][CH3:35])=[N:32][C:31]([CH3:36])=[CH:30][N:29]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=O)C(C)C.C[O-].[Na+]>CO>[CH3:27][O:26][C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:13]2[C:12]([S:9]([NH:8][C:28]3[C:33]([O:34][CH3:35])=[N:32][C:31]([CH3:36])=[CH:30][N:29]=3)(=[O:10])=[O:11])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:23][CH:22]=1)=[O:25]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22325614Methyl 4-(3-{[(3-Methoxy-5-Methylpyrazin-2-yl)[(2-Methylpropoxy)carbonyl]aMino]sulfonyl}pyridin-2-yl)benzoate

Product 1

HCID 211863122-(4-methoxycarbonylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideYield 28.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(isobutoxycarbonyl)-2-(4-methoxycarbonylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (830 mg) and sodium methoxide (433 mg) in methanol (25 ml) was heated under reflux for 1 hour. Volatile material was removed by evaporation and saturated ammonium chloride solution (20 ml) was added to the residue. The mixture was extracted with ethyl acetate (2×20 ml) and the extracts were washed with water (2×15 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with 25-50% ethyl acetate/hexane, to give 2-(4-methoxycarbonylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (190 mg), m.p. 144-146° C.; microanalysis found: C, 55.2; H, 4.3; N, 13.3%; C23H24BrN4O4S requires: C, 55.1; H, 4.4; N, 13.5%.

Workup

  1. temperatureunder reflux for 1 hour
  2. customVolatile material was removed by evaporation and saturated ammonium chloride solution (20 ml)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (2×20 ml)
  5. washthe extracts were washed with water (2×15 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed by evaporation
  8. customthe residue was purified by flash chromatography
  9. washeluting with 25-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-beea5354b3554ea49b25e8a6f34be7ca
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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