2-(4-METHYLPIPERAZINO)-3-PYRIDINAMINE Chemical Properties

Melting point:

112-114°C

Boiling point:

361.6±42.0 °C(Predicted)

Density 

1.142±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.35±0.29(Predicted)

Appearance

Off-white to pink Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933599590

2-(4-METHYLPIPERAZINO)-3-PYRIDINAMINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-(4-methylpiperazinyl)-3-aminopyridine from 1-methyl-4-(3-nitro-2-pyridinyl)piperazine: preparation of 2-(4-methylpiperazin-1-yl)-3-nitropyridine (PP26, 0.50 g, 2.25 mmol), ammonium formate (1.00 g, 15.85 mmol) and 10% Pd/C (0.050 g) ) solution in methanol (20 mL). The reaction mixture was stirred at room temperature for 1 h. The filtrate was subsequently filtered through diatomaceous earth (Celite?) and concentrated. The residue was dissolved in ethyl acetate, washed sequentially with aqueous potassium carbonate and brine, dried over anhydrous magnesium sulfate and concentrated to give 0.35 g (81% yield) of 2-(4-methylpiperazinyl)-3-aminopyridine (PP24) as a violet oil, which was used directly in the next reaction without further purification. The product was confirmed by NMR hydrogen spectroscopy (CDCl3): δ 7.77 (dd, J = 4.6, 1.7 Hz, 1H), 6.90 (dd, J = 7.5, 1.7 Hz, 1H), 6.79 (dd, J = 7.9, 5.0 Hz, 1H), 3.71 (br s, 2H), 3.15 (br s, 4H), 2.57 (br s, 4H) , 2.34 (s, 3H).

References

[1] Patent: WO2006/48727, 2006, A1. Location in patent: Page/Page column 72-73
[2] Patent: WO2013/40215, 2013, A1. Location in patent: Paragraph 00304
[3] Patent: WO2018/75858, 2018, A1. Location in patent: Paragraph 0335; 0337

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