Citric Acid → HCID 86619567, compound

HRID 1929822Notes

Reaction equation

HRID 1929822 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:7]([NH2:10])=[N:8][CH:9]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22]Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Br:3][C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:7]([N:10]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 86619566HCID 86619566, compound

Product 1

HCID 86619567HCID 86619567, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.55 g) is added at room temperature to a solution of 5-bromo-3-(2-chloro-phenyl)-pyrazin-2-ylamine (0.23 g) in DMF (10 mL). Subsequently 1-bromo-4-chlorobutane (0.21 g) is added and the mixture is stirred for 3 h. Citric acid (10%, 20 mL) is added and the mixture is extracted with ethyl acetate (3×50 mL). Organic phases were pooled, washed with sodium bicarbonate and brine, dried with Na2SO4 and the solvent was evaporated. The residue was purified by chromatography on silica gel with heptane/ethyl acetate 2:1 to yield 0.27 g of the title compound as a yellow oil, MS (ISP) 338.1, 340.0 (M+H)+.

Workup

  1. extractionthe mixture is extracted with ethyl acetate (3×50 mL)
  2. washwashed with sodium bicarbonate and brine
  3. dry with materialdried with Na2SO4
  4. customthe solvent was evaporated
  5. customThe residue was purified by chromatography on silica gel with heptane/ethyl acetate 2:1

Sources & evidence

ORD record
ord-16450b380ffa470e8a7818663241c08e
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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