Ammonium Hydroxide → 2-[5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetamide

HRID 1992639Notes

Reaction equation

HRID 1992639 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[N:7][CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:10]=1.[NH4+:22].[OH-]>>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:9]2[CH:10]=[C:5]([CH2:4][C:3]([NH2:22])=[O:2])[C:6]([N+:18]([O-:20])=[O:19])=[N:7][CH:8]=2)[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 66869293[5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetic acid methyl ester

Product 1

HCID 668689562-[5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetamide

Procedure

A solution of [5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetic acid methyl ester (222 mg, 0.75 mmol) in 33% aq. NH4OH (100 mL) is stirred for 16 h at 50° C. in a sealed autoclave. TLC analysis indicated complete consumption of starting material. The solvent is evaporated at reduced pressure to afford the title compound as a yellow solid in a 3:2 mixture with the corresponding carboxylic acid. 1H NMR (d6-DMSO 400 MHz): δ 2.18 (s, 3H), 2.36-2.44 (m, 4H), 3.36-3.44 (m, 4H), 3.77 (s, 2H), 6.92 (bs, 1H), 7.34 (d, J=2 Hz, 1H), 7.44 (bs, 1H), 8.07 (d, J=2 Hz, 1H). ES+−MS: 280.4 [M+H]+.

Workup

  1. customconsumption of starting material
  2. customThe solvent is evaporated at reduced pressure

Sources & evidence

ORD record
ord-5844e896d4f64e84bdbb1f8a31478ecb
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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