Piperidine → tert-Butyl 7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 517906Notes

Reaction equation

HRID 517906 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13]2=[N:14][C:15]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[N:17]=[C:12]2[CH2:11][CH:10](OC(=O)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>O>[N:36]1([CH:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C:13]3=[N:14][C:15]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)=[C:16]([C:18]4[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=4)[N:17]=[C:12]3[CH2:11]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 89690147tert-Butyl-7-acetoxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 89690064tert-Butyl 7-(piperidin-1-yl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl-7-acetoxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 5)(210 mg, 0.443 mmol) was treated with piperidine (4380 μl, 44.3 mmol). The resulting pale yellow suspension was sonicated and then stirred at room temperature overnight. The resulting solution was added to water (100 ml) and extracted with DCM (×3), passing the organic extracts through a phase separating column. The filtrate was concentrated under reduced pressure and purification of the crude material by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. customThe resulting pale yellow suspension was sonicated
  2. extractionextracted with DCM (×3)
  3. customseparating column
  4. concentrationThe filtrate was concentrated under reduced pressure and purification of the crude material by chromatography on silica eluting with 0-40% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-9a5c230cf34d4d738be8a169386d61e4
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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