Methanol → HCID 21186257, compound

HRID 361442Notes

Reaction equation

HRID 361442 reaction equation
[H-].[Na+].[H][H].Br[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([S:19]([N:22](C(OCC(C)C)=O)[C:23]3[C:28]([O:29][CH3:30])=[N:27][C:26]([CH3:31])=[CH:25][N:24]=3)(=[O:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.[CH3:39][OH:40]>>[CH3:39][O:40][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([S:19]([NH:22][C:23]3[C:28]([O:29][CH3:30])=[N:27][C:26]([CH3:31])=[CH:25][N:24]=3)(=[O:20])=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 211862832-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 21186257HCID 21186257, compound

Procedure

Oil-free sodium hydride (240 mg) was added to methanol (20 ml) with stirring. When evolution of hydrogen ceased, 2-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (549 mg) was added and the mixture was stirred for 2 hours. Volatile material was removed by evaporation and saturated ammonium chloride solution (10 ml) was added to the residue. The mixture was extracted with ethyl acetate (3×20 ml) and the extracts were dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (13:7 v/v), to give 2-(4-methoxymethylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (170 mg), m.p. 129°-130° C. (after trituration with ether); microanalysis found: C, 56.9; H, 4.9; N, 13.9%; C19H20N4O4S requires: C, 57.0; H, 5.0; N, 14.0%.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customVolatile material was removed by evaporation and saturated ammonium chloride solution (10 ml)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  5. dry with materialthe extracts were dried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (13:7 v/v)

Sources & evidence

ORD record
ord-c43e7b9c503844a381278ac132142965
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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