5-(4-Methylpiperazin-1-yl)pyridin-2-amine Chemical Properties

Melting point:

148 °C

Boiling point:

368.1±42.0 °C(Predicted)

Density 

1.142±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Water (Slightly)

form 

powder to crystal

pka

7.41±0.42(Predicted)

color 

Light yellow to Brown

Stability:

Hygroscopic

InChI

InChI=1S/C10H16N4/c1-13-4-6-14(7-5-13)9-2-3-10(11)12-8-9/h2-3,8H,4-7H2,1H3,(H2,11,12)

InChIKey

QDMPMBFLXOWHRY-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(N2CCN(C)CC2)C=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

5-(4-Methylpiperazin-1-yl)pyridin-2-amine Usage And Synthesis

Description

5-(4-Methylpiperazin-1-yl)pyridin-2-amine is a pharmaceutical intermediate compound that can be used to prepare trilaciclib. Trilaciclib is the first intravenous CDK4/6 inhibitor approved by the FDA for reducing the risk of bone marrow suppression (i.e. decreased red blood cells, white blood cells, and platelets) in adult patients with small cell lung cancer (SCLC) caused by specific chemotherapy drugs.

Chemical Properties

Light yellow to Brown powder to crystal.

Uses

5-(4-Methylpiperazin-1-yl)pyridin-2-amine can be used for chemical mechanical planarization for tungsten-containing substrates.

Synthesis

General procedure for the synthesis of 1-methyl-4-(6-aminopyridin-3-yl)piperazine from 1-methyl-4-(6-nitropyridin-3-yl)piperazine: a mixture of 1-methyl-4-(6-nitropyridin-3-yl)piperazine (1.11 g, 5.02 mmol) and 10% Pd/C (110 mg) in methanol (15 mL) was stirred for 5 h at room temperature . Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford 951 mg (99% yield) of a yellow solid product, 1-methyl-4-(6-aminopyridin-3-yl)piperazine, which could be used in the subsequent reaction without further purification. The 1H NMR (CDCl3) data of the product were as follows: δ 7.78 (d, 1H, J = 3.0 Hz), 7.18 (dd, 1H, J = 3.0, 8.9 Hz), 6.48 (d, 1H, J = 8.9 Hz), 3.08 (dd, 4H, J = 4.9, 4.9 Hz), 2.61 (dd, 4H, J = 4.9, 4.9 Hz) , 2.37 (s, 3H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1892 - 1915
[2] Patent: US2005/38078, 2005, A1. Location in patent: Page/Page column 29
[3] Patent: WO2004/14904, 2004, A1. Location in patent: Page 51
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 348 - 364
[5] Patent: US2017/313683, 2017, A1. Location in patent: Paragraph 0300-0301

5-(4-Methylpiperazin-1-yl)pyridin-2-amine(571189-49-6)Related Product Information

• tert-Butyl 4-(6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido(2,3-d)pyrimidin-2-ylamino)-pyridin-3-yl)-piperazine-1-carboxylate
• 5-(4-Methylpiperazin-1-yl)pyridin-2-amine
• 5-(4-ethylpiperazin-1-yl)pyridin-2-amine
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• OTAVA-BB 1119890
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• OTAVA-BB 1119894
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