Heptanoic acid, 7-oxo-, ethyl ester → Ethyl 7-(2-phenyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 406189Notes

Reaction equation

HRID 406189 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[CH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C([O-])(O)=O.[Na+]>[C:1]1([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[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:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 666662562-Phenyl-3-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 66665828Ethyl 7-(2-phenyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-phenyl-3-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate FA) (1.03 g, 3.42 mmol) in 1,2-dichloroethane (15 ml) was treated with ethyl 7-oxoheptanoate (1.776 g, 10.25 mmol) followed by sodium triacetoxyborohydride (3.62 g, 17.09 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with saturated NaHCO3 (70 ml) and was extracted with DCM (×3). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The resulting crude product was purified by chromatography on silica eluting with 0-60% EtOAc/iso-hexane to give an oil. The product was loaded onto an Isolute™ SCX-2 cartridge, washed with MeOH and eluted with 2M NH3 in MeOH. The methanolic ammonia fractions were concentrated in vacuo to afford the title compound;

Workup

  1. extractionwas extracted with DCM (×3)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified by chromatography on silica eluting with 0-60% EtOAc/iso-hexane
  6. customto give an oil
  7. washwashed with MeOH
  8. washeluted with 2M NH3 in MeOH
  9. concentrationThe methanolic ammonia fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-17b99eb094e844d38e173464855593cd
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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