Potassium Carbonate → Ethyl 7-(2-bromo-3-chloro-6-oxo-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 517929Notes

Reaction equation

HRID 517929 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:5]2=[N:6][C:7]=1[Cl:8].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]2=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 866818522-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one

Product 1

HCID 86681853Ethyl 7-(2-bromo-3-chloro-6-oxo-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-3-chloro-7,8-dihydro-5H-pyrido[2,3-b]pyrazin-6-one (prepared according to the preparation procedures disclosed in PCT patent application PCT/EP2011/062028, Intermediate J) (3.9 g, 14.86 mmol) and ethyl 7-bromoheptanoate (7.05 g, 29.7 mmol) in DMF (75 ml) under a nitrogen atmosphere was treated with potassium carbonate (10.27 g, 74.3 mmol) and the resulting solution was stirred at room temperature for 4 days. The mixture was diluted with water and extracted with EtOAc (×2). The extracts were washed with water and brine, dried (MgSO4) and evaporated under vacuum. The crude product was purified by chromatography on silica eluting with 0-60% EtOAc in iso-hexane to afford the titled compound;

Workup

  1. customaccording to the preparation procedures
  2. extractionextracted with EtOAc (×2)
  3. washThe extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under vacuum
  6. customThe crude product was purified by chromatography on silica eluting with 0-60% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-958e6fc05c9443f5864245f699942dad
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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