Triethylamine → Ethyl 7-(2,3-bis(3-fluoro-4-methylphenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 406193Notes

Reaction equation

HRID 406193 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH2:26][CH2:25][CH2:24][NH:23][C:12]3=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].O=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH2:26][CH2:25][CH2:24][N:23]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:12]3=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 77609Heptanoic acid, 7-oxo-, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 666661992,3-Bis(3-fluoro-4-methylphenyl)-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Product 1

HCID 66666003Ethyl 7-(2,3-bis(3-fluoro-4-methylphenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2,3-bis(3-Fluoro-4-methylphenyl)-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate G)(256 mg, 0.729 mmol) in DCE (10 ml) was treated with ethyl 7-oxoheptanoate (125 mg, 0.729 mmol) and triethylamine (0.112 ml, 0.801 mmol) and stirred at RT for 15 mins. Sodium triacetoxyborohydride (772 mg, 3.64 mmol) was added and stirring continued at 60° C. for 18 h. The reaction mixture was diluted with water and DCM and the organic portion was separated. The aqueous portion was extracted with DCM and the combined organic extracts were dried (sodium sulphate), filtered and concentrated in vacuo to give a yellow gum. The crude product was purified by chromatography on silica eluting with 0-20% EtOAc in iso-hexane to afford the title compound;

Workup

  1. stirringstirring
  2. waitcontinued at 60° C. for 18 h
  3. customthe organic portion was separated
  4. extractionThe aqueous portion was extracted with DCM
  5. dry with materialthe combined organic extracts were dried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow gum
  9. customThe crude product was purified by chromatography on silica eluting with 0-20% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-526dceb81da543ee837db8a3b1268c3e
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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