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

HRID 2276569Notes

Reaction equation

HRID 2276569 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)-one2×

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 (Intermediate J) (3.9 g, 14.86 mmol) and ethyl 7-bromoheptanoate (7.05 g, 29.7 mmol) in DMF (75 ml) under nitrogen was treated with potassium carbonate (10.27 g, 74.3 mmol) and the resultant solution was stirred at room temperature for 96 hours. The mixture was diluted with water and extracted with EtOAc (×2). The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-60% EtOAc/iso-hexane 0-60% afforded the title compound;

Workup

  1. extractionextracted with EtOAc (×2)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude product by chromatography on silica eluting with 0-60% EtOAc/iso-hexane 0-60%

Sources & evidence

ORD record
ord-6b55bbcae332468c94aa0f3ac052ebea
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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