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

Product Name4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide
CAS139756-02-8
MFC8H14N4O
MW182.22
EINECS604-160-8
MOL File139756-02-8.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

A potent hypolipidemic agent. A possible inhibitor of phosphodiesterase 1

Uses

An impurity in the synthesis of Sildenafil.

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

1-Methyl-4-nitro-3-propyl-(1H)-pyrazole-5-carboxamide

139756-01-7

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

139756-02-8

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

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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