[2-(4-Methyl-piperazin-1-yl)-5-nitro-pyridin-4-yl]-acetic acid ethyl ester → [5-Amino-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid ethyl ester

HRID 1992655Notes

Reaction equation

HRID 1992655 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][N:9]=[C:8]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:7]=1)[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[C:11]([NH2:12])=[CH:10][N:9]=[C:8]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 66869335[2-(4-Methyl-piperazin-1-yl)-5-nitro-pyridin-4-yl]-acetic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 66869297[5-Amino-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[2-(4-Methyl-piperazin-1-yl)-5-nitro-pyridin-4-yl]-acetic acid ethyl ester (2.78 g, 9.02 mmol) is dissolved in MeOH (28 ml). Palladium on carbon (10%, 96 mg, 0.90 mmol) is added, and the reaction flask is connected to a balloon filled with hydrogen. After vigorous stirring for 2.5 h, TLC analysis indicated complete conversion. The reaction mixture is filtered, the organic solvent removed, and the residue purified by FCC (CH2Cl2/MeOH, gradient from 97:3 to 70:30) to yield [5-amino-2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-acetic acid ethyl ester. 1H NMR (CDCl3, 400 MHz): δ 1.27 (t, J=7 Hz, 3H), 2.35 (s, 3H), 2.54 (m, 4H), 3.40 (m, 4H), 3.55 (s, 2H), 3.62 (s, broad, 2H), 4.16 (q, J=7 Hz, 2H), 6.50 (s, 1H), 7.79 (s, 1H). ES+−MS: 279.3 [M+H]+.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe organic solvent removed
  3. customthe residue purified by FCC (CH2Cl2/MeOH, gradient from 97:3 to 70:30)

Sources & evidence

ORD record
ord-065ef05825d24b67967ff46036a15454
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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