Diethyl Ether → HCID 18704778, compound

HRID 2287383Notes

Reaction equation

HRID 2287383 reaction equation
C([N-]C(C)C)(C)C.[Li+].[NH2:9][C:10]1[C:15]([N:16]([CH3:18])[CH3:17])=[N:14][C:13]([Br:19])=[CH:12][N:11]=1.[CH3:20][N:21]([CH3:36])[C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH:24]=[CH:25][CH:26]=[C:27]2[S:32](Cl)(=[O:34])=[O:33].CCOCC>O1CCCC1>[CH3:20][N:21]([CH3:36])[C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH:24]=[CH:25][CH:26]=[C:27]2[S:32]([NH:9][C:10]1[C:15]([N:16]([CH3:17])[CH3:18])=[N:14][C:13]([Br:19])=[CH:12][N:11]=1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11801Dansyl chlorideHCID 2724682Lithium diisopropylamideHCID 142076275-Bromo-N~3~,N~3~-dimethylpyrazine-2,3-diamine

Product 1

HCID 18704778HCID 18704778, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

A 2M solution of lithium diisopropylamide in tetrahydrofuran (THF)/heptane (1:1 v/v; 2.3 ml) was added over 10 minutes to a stirred solution of 2-amino-5-bromo-3-dimethylaminopyrazine (0.45 g) in dry THF (25 ml) at -60° C. The solution was stirred at -60° C. for 1 hour and then 5-dimethylamino-1-naphthalenesulphonyl chloride (0.62 g) was added portionwise over 5 minutes. The solution was allowed to warm to ambient temperature and then stirred for 18 hours. Ether (20 ml) was added and the solution was extracted with water (2×20 ml). The aqueous extracts were neutralised to pH 7 with 10% citric acid solution and extracted with ethyl acetate (2×20 ml). The organic extracts were combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column. The resulting solid was further purified by elution with dichloromethane through a fresh silica gel Mega Bond Elut column to give 5-dimethylamino-N-(5-bromo-3-dimethylamino-2-pyrazinyl)-1-naphthalenesulphonamide (0.125 g), m.p. 180-182° C. (after trituration with ether); mass spectrum (+ve FAB, methanol/dichloromethane/DMSO/NBA): 450 (M+H)+.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 18 hours
  3. extractionthe solution was extracted with water (2×20 ml)
  4. extractionextracted with ethyl acetate (2×20 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column
  8. customThe resulting solid was further purified by elution with dichloromethane through a fresh silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-a4c2d4a5cf2f45adaf8ba67df6c928f6
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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