Sodium Hydroxide → HCID 18704812, compound

HRID 343388Notes

Reaction equation

HRID 343388 reaction equation
C(O[C:9]([N:11]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[C:18]2[S:23]([NH:26][C:27]1[C:32]([O:33][CH3:34])=[N:31][C:30]([Br:35])=[CH:29][N:28]=1)(=[O:25])=[O:24])[CH3:12])=O)C1C=CC=CC=1.[OH-].[Na+]>Br.C(O)(=O)C.O>[CH2:9]([N:11]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[C:18]2[S:23]([NH:26][C:27]1[C:32]([O:33][CH3:34])=[N:31][C:30]([Br:35])=[CH:29][N:28]=1)(=[O:25])=[O:24])[CH3:12])[C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:14]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 10578729HCID 10578729, compound

Product 1

HCID 18704812HCID 18704812, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

5-(N-Benzyloxycarbonyl-N-methylamino)-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.40 g) was suspended in 33% hydrobromic acid in acetic acid (5 ml) and the mixture was stirred for 1 hour. Evaporation afforded a yellow residue which was dissolved in water (20 ml), basified to pH 10 with 1N aqueous sodium hydroxide and extracted with ethyl acetate (3×25 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (30 g), eluting with a gradient of 20-50% ethyl acetate in hexane, affording 5-(N-benzyl-N-methylamino)-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.095 g); 1H NMR (d6 -DMSO): 2.72 (s,3H), 3.90 (s,3H), 4.25 (s,2H), 7.2-7.4 (m,6H), 7.58 (t,1H), 7.68 (t,1H), 7.80 (s,1H), 8.32 (dd,1H), 8.46 (d,1H), 8.64 (d,1H), 11.48 (br,1H); mass spectrum (+ve FAB, methanol/NBA); 513(M+H)+.

Workup

  1. customEvaporation
  2. customafforded a yellow residue which
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (30 g)
  7. washeluting with a gradient of 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2576c09661184372bc7a401d8af6d2a5
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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