Citric Acid → HCID 10550094, compound

HRID 343363

Reaction equation

HRID 343363 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([CH3:10])=[N:8][C:7]([Br:11])=[CH:6][N:5]=1.[CH3:12][N:13]([CH3:28])[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[C:19]2[S:24](Cl)(=[O:26])=[O:25].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>COCCOC>[CH3:12][N:13]([CH3:28])[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[C:19]2[S:24]([NH:3][C:4]1[C:9]([CH3:10])=[N:8][C:7]([Br:11])=[CH:6][N:5]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 217851475-Bromo-3-methylpyrazin-2-amine

Product 1

HCID 10550094HCID 10550094, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 0.1 g) was added portionwise to a stirred solution of 2-amino-5-bromo-3-methylpyrazine (0.188 g) in 1,2-dimethoxyethane (DHE; 4 ml). After 5 minutes 5-dimethylamino-1-naphthalenesulphonyl chloride (0.3 g) was added, in a single portion, and the reaction was allowed to a stir for 18 hours. 2M Aqueous citric acid solution (10 ml) was added and the reaction was extracted with dichloromethane (3×25 ml). The combined extracts were dried (MgSO4) and evaporated to give a brown oil. The oil was purified by chromatography on silica gel, eluting with dichloromethane/diethyl ether (1:1) to give 5-dimethylamino-N-(5-bromo-3-methyl-2-pyrazinyl)-1-naphthalenesulphonamide as a cream solid (0.138 g, 33%), m.p. 171°-172° C.; mass spectrum (+ve FAB, DMSO/methanol/NBA): 421 (M+H)+.

Workup

  1. extractionthe reaction was extracted with dichloromethane (3×25 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customto give a brown oil
  5. customThe oil was purified by chromatography on silica gel
  6. washeluting with dichloromethane/diethyl ether (1:1)

Sources & evidence

ORD record
ord-40c9a0200be94b7d93d324fb8af3ca89
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Linked notes

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