Hydrogen chloride-ethyl acetate → 4-(2-(4-aminopiperidin-1-yl)ethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one hydrochloride

HRID 1510637Notes

Reaction equation

HRID 1510637 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.[ClH:30].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:30].[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

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57815384tert-Butyl {1-[2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 689298784-(2-(4-aminopiperidin-1-yl)ethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.23 g of tert-butyl (1-(2-(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)carbamate in 3 mL of ethyl acetate, 4.0 mL of a 4.0 mol/L hydrogen chloride/ethyl acetate solution was added at room temperature. The mixture was stirred at the same temperature for 5 hours, and then left overnight. The solvent was distilled off under reduced pressure, diethyl ether was added to the resultant residue, and the solid was filtered off to obtain 0.23 g of 4-(2-(4-aminopiperidin-1-yl)ethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one hydrochloride as a light brown solid.

Workup

  1. additionwas added at room temperature
  2. waitleft overnight
  3. distillationThe solvent was distilled off under reduced pressure, diethyl ether
  4. additionwas added to the resultant residue
  5. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-3fbc93fae14443c6afef2c2144a6235a
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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