Water → HCID 22710697, compound

HRID 352920Notes

Reaction equation

HRID 352920 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[N:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:48]=[CH:47][C:34]([C:35](OC3C=CC([N+]([O-])=O)=CC=3)=[O:36])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]([C:35](=[O:36])[C:34]3[CH:33]=[CH:32][C:31]([C:28]4[CH:27]=[CH:26][N:25]=[CH:30][CH:29]=4)=[CH:48][CH:47]=3)[CH2:17][CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22710404HCID 22710404, compoundHCID 22711147HCID 22711147, compound

Product 1

HCID 22710697HCID 22710697, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In N,N-dimethylformamide (1 ml), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-6-methoxycarbonyl-1,2,3,4-tetrahydropyrazine (60 mg) and p-nitrophenyl 4-(pyridin-4-yl)benzoate (52 mg) were dissolved, followed by the addition of sodium hydride (60% in oil, 7.20 mg) under ice cooling. The resulting mixture was stirred for 1 hour. Water and ethyl acetate were added to the reaction mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (ethyl acetate:hexane=2:1), followed by dissolution in ethanol. To the resulting solution, 1N aqueous hydrochloric acid in ethanol was added and the resulting mixture was concentrated, whereby the title compound (58 mg, 60%) was obtained as pale yellow powder.

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (ethyl acetate:hexane=2:1)
  5. dissolutionfollowed by dissolution in ethanol
  6. additionTo the resulting solution, 1N aqueous hydrochloric acid in ethanol was added
  7. concentrationthe resulting mixture was concentrated

Sources & evidence

ORD record
ord-5b88af2d63504edf852cd1e633778e32
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…