Ammonium Chloride → N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 1384238Notes

Reaction equation

HRID 1384238 reaction equation
C(OCC(C)OCC1C=CC([C:16]2[C:21]([S:22]([NH:25][C:26]3[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)=CC=1)(C)(C)C.[Cl-].[NH4+]>FC(F)(F)C(O)=O>[CH3:33][O:32][C:31]1[C:26]([NH:25][S:22]([C:21]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:23])=[O:24])=[N:27][CH:28]=[C:29]([CH3:34])[N:30]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 211862852-{4-[(2-tert-butoxy-1-methylethoxy)methyl]phenyl}-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

Product 1

HCID 23226620N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideYield 59.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-{4-[(2-tert-butoxy-1-methylethoxy)methyl]phenyl}-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (248 mg) in trifluoroacetic acid (1 ml) was left to stand for 30 minutes. Saturated ammonium chloride solution (20 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The extracts were dried (MgSO4) and concentrated and the residue was dissolved in dichloromethane (10 ml). The solution was washed with water (2×10 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/ethyl acetate (1:24 v/v), to give 2-[4-([2-hydroxy-1-methyl)ethoxy]methyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (82 mg), 1H NMR (d6-DMSO): 1.15 (s, 3H), 2.25 (s, 3H), 3.3-3.7 (s, 3H), 3.8 (s, 3H), 4.6 (s, 2H), 7.3-7.55 (m, 5H), 7.6 (dd, 1H), 8.45 (dd, 1H), 8.8 (dd, 1H), 10.35-10.45 (br s, 1H); mass spectrum (+ve ESP): 445 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in dichloromethane (10 ml)
  5. washThe solution was washed with water (2×10 ml)
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified by flash chromatography
  9. washeluting with methanol/ethyl acetate (1:24 v/v)

Sources & evidence

ORD record
ord-2ab6f79de816465b9c33eba36f605d70
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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