Nitrogen → Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 517879Notes

Reaction equation

HRID 517879 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]1[N:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:14]2=[N:15][C:16]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:18]=[C:13]2[CH2:12][CH2:11]1)[CH3:2].N#N>CCO>[CH2:1]([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:14]2=[N:15][C:16]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:18]=[C:13]2[CH2:12][CH2:11]1)[CH3:2]

Participants

4

Reactant 2

HCID 947NitrogenHCID 131733355tert-Butyl 6-(6-ethoxy-6-oxohex-2-enyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 89690447Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 6-(6-ethoxy-6-oxohex-2-enyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 3) (88 mg, 0.158 mmol) in EtOH (3 ml) was degassed with N2 and treated with 10% Pd(C) (1.685 mg, 0.016 mmol). The resulting black suspension was stirred at room temperature under an atmosphere of hydrogen for 16 hours. The resulting mixture was filtered through a pre-packed 2.5 g Celite® column eluting with EtOH. The filtrate concentrated under reduced pressure to afford the titled compound as a yellow oil:

Workup

  1. filtrationThe resulting mixture was filtered through a pre-packed 2.5 g Celite® column
  2. washeluting with EtOH
  3. concentrationThe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-03a48c4c5ddb46b4bb2c34606b1f2673
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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