4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide Chemical Properties

Melting point:

98-101 °C(lit.)

Boiling point:

325.9±42.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Ethyl Acetate, Methanol

form 

Solid

pka

15.30±0.50(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C8H14N4O/c1-3-4-5-6(9)7(8(10)13)12(2)11-5/h3-4,9H2,1-2H3,(H2,10,13)

InChIKey

PZMXDLWWQHYXGY-UHFFFAOYSA-N

SMILES

N1(C)C(C(N)=O)=C(N)C(CCC)=N1

CAS DataBase Reference

139756-02-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933.19.4300

MSDS

• Language:English Provider:SigmaAldrich

4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

An impurity in the synthesis of Sildenafil.

Uses

A potent hypolipidemic agent. A possible inhibitor of phosphodiesterase 1

Definition

ChEBI: 4-amino-1-methyl-3-propylpyrazole-5-carboxamide is a multi-substituted pyrazolecarboxamide used in the industrial synthesis of sildenafil. It is a member of pyrazoles and a monocarboxylic acid amide.

Synthesis

Step 7 Synthesis of 4-amino-1-methyl-3-n-propyl-1H-pyrazole-5-carboxamide: 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxamide (14.7 g, 69.3 mmol) was suspended in ethyl acetate (130 mL) and 10% palladium/carbon catalyst (3.3 g) was added. The reaction mixture was stirred overnight at 50 °C and 4 atm hydrogen pressure. Upon completion of the reaction, it was cooled to room temperature, the catalyst was removed by filtration, and the catalyst was washed with ethyl acetate. The combined filtrates were dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 4-amino-1-methyl-3-n-propyl-1H-pyrazole-5-carboxamide (13.8 g, 98% yield) as a white solid. The product was confirmed by 1H NMR (300 MHz, CDCl3): δ 4.12 (s, 3H), 2.84 (s, 2H), 2.55 (t, 2H, J = 7.2 Hz), 1.71-1.61 (m, 2H), 0.99 (t, 3H, J = 7.2 Hz); LC-MS showed m/z = 183 (MH)+.

References

[1] Patent: US2008/194529, 2008, A1. Location in patent: Page/Page column 57
[2] Patent: WO2014/131855, 2014, A1. Location in patent: Page/Page column 81
[3] Patent: WO2016/20307, 2016, A1. Location in patent: Page/Page column 51
[4] Patent: CN103044330, 2018, B. Location in patent: Paragraph 0025; 0031-0032; 0034-0035
[5] Patent: WO2015/114647, 2015, A1. Location in patent: Page/Page column 47; 48

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