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

HRID 517881Notes

Reaction equation

HRID 517881 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.CCOCC>[O:24]=[C:21]1[N:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:10]2=[N:11][C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:25])=[CH:6][CH:5]=3)[N:8]=[C:9]2[CH2:23][CH2:22]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 666655132,3-Dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one

Product 1

HCID 66665730Ethyl 7-(6-oxo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A yellow solution of 2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-6(5H)-one ((prepared according to the preparation procedures disclosed in PCT patent application PCT/EP2011/062028, Example 12.1 step 1) (2.0 g, 6.07 mmol) and ethyl 7-bromoheptanoate (2.88 g, 12.14 mmol) in DMF (40 ml) under a nitrogen atmosphere was treated with potassium carbonate (4.20 g, 30.4 mmol) and the resulting suspension was stirred at room temperature for 23 hours. The mixture was diluted with water and extracted with EtOAc (×2). The extracts were washed with water (×2) and brine, dried (MgSO4) and evaporated under reduced pressure to afford a yellow oil. The crude material was diluted with ether (50 ml) and washed with water (2×20 ml), brine, dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. customaccording to the preparation procedures
  2. extractionextracted with EtOAc (×2)
  3. washThe extracts were washed with water (×2) and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto afford a yellow oil
  7. washwashed with water (2×20 ml), brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customPurification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-094db212915f4cb9865d4d649f7a22d8
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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