Methanol → 4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 656963Notes

Reaction equation

HRID 656963 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][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]3)[C:7]=2[N:29]=1.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O.CO>C(Cl)Cl.FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:8]2[C:9](=[O:12])[CH:10]=[N:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:29][C:7]2=3)[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 887MethanolHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 57815384tert-Butyl {1-[2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 578153944-[2-(4-Aminopiperidin-1-yl)ethyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-dimethylethyl (1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-4-piperidinyl)carbamate (470 mg, 1.2 mmol) in DCM/trifluoroacetic acid (10 ml/10 ml) was stirred at rt for 30 minutes then evaporated to dryness. The residue was triturated with ether and then resultant solid dried in vacuo. The solid was dissolved in DCM/MeOH (20 ml/20 ml) and treated with MP-carbonate resin (2.3 mmol of carbonate per gram, 3 g, ca 8 mmol). After 1.5 hours the mixture was filtered, washing alternatively with small volumes of DCM and MeOH. The combined filtrates were evaporated affording a yellow oil (contaminated with particulate material from the resin). This residue was treated with 20% MeOH in DCM (20 ml) filtered and evaporated affording a yellow oil (350 mg, 100%).

Workup

  1. customthen evaporated to dryness
  2. customThe residue was triturated with ether
  3. customresultant solid dried in vacuo
  4. dissolutionThe solid was dissolved in DCM/MeOH (20 ml/20 ml)
  5. filtrationAfter 1.5 hours the mixture was filtered
  6. washwashing alternatively with small volumes of DCM and MeOH
  7. customThe combined filtrates were evaporated
  8. customaffording a yellow oil (
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-524abaeadad549aab6cf86cb5d27a6ae
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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