Diethyl Ether → HCID 18704787, compound

HRID 343390Notes

Reaction equation

HRID 343390 reaction equation
C(OC([NH:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[C:17]2[S:22]([NH:25][C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([Br:34])=[CH:28][N:27]=1)(=[O:24])=[O:23])=O)C1C=CC=CC=1.C(OCC)C>Br.C(O)(=O)C>[NH2:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[C:17]2[S:22]([NH:25][C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([Br:34])=[CH:28][N:27]=1)(=[O:23])=[O:24]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 18704806HCID 18704806, compound

Product 1

HCID 18704787HCID 18704787, compoundYield 13.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

5-(N-Benzyloxycarbonylamino)-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.7 g) was dissolved in 33% hydrobromic acid in acetic acid (14 ml) and the resulting solution was stirred for 1 hour. Diethyl ether (60 ml) was added and after 10 minutes further stirring, the mixture was filtered. The solid was dissolved in water (5 ml), basified to pH 8 by the addition of 1N aqueous sodium hydroxide and extracted with ethyl acetate (3×25 ml). The combined organic extracts were evaporated and the residue was purified by flash chromatography on silica gel (10 g), eluting with a gradient of 20-50% ethyl acetate in hexane to give 5-amino-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.07 g); 1H NMR (d6 -DMSO): 3.82 (s,3H), 6.78 (d,1H), 7.35 (t,1H), 7.50 (t,1H), 7.78 (s,1H), 7.91 (d,1H), 8.25 (d,1H), 8.40 (d,1H); mass spectrum (+ve FAB, methanol/NBA): 409 (M+H)+.

Workup

  1. stirringfurther stirring
  2. filtrationthe mixture was filtered
  3. dissolutionThe solid was dissolved in water (5 ml)
  4. additionbasified to pH 8 by the addition of 1N aqueous sodium hydroxide
  5. extractionextracted with ethyl acetate (3×25 ml)
  6. customThe combined organic extracts were evaporated
  7. customthe residue was purified by flash chromatography on silica gel (10 g)
  8. washeluting with a gradient of 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-685f88852abe4a5f97dc5beb6be3d585
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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