Sodium Sulfate → tert-Butyl {1-[2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 657110Notes

Reaction equation

HRID 657110 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH:14]=O)[C:7]=2[N:16]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:17]3[CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22]3)[C:7]=2[N:16]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 57815220(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde

Product 1

HCID 57815384tert-Butyl {1-[2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamateYield 59%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

[6-(Methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]acetaldehyde (0.250 g, 1.14 mmol) was combined with 1,1-dimethylethyl 4-piperidinylcarbamate (0.229 g, 1.14 mmol) in a 1:1 MeOH/DCM solution. Excess Na2SO4 was added as a drying agent and the solution was stirred at ambient temperature overnight. NaBH(OAc)3 (0.724 g, 3.42 mmol) was added and the reaction was stirred an additional 2 h. The solution was concentrated onto silica gel under vacuum and the crude residue purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired compound (0.271 g, 59%).

Workup

  1. stirringthe reaction was stirred an additional 2 h
  2. concentrationThe solution was concentrated onto silica gel under vacuum
  3. customthe crude residue purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-d4120fcdd93b4ebfa18fdad2d6f29a3e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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