ChemicalBook CAS DataBase List 139756-02-8

139756-02-8

Name	4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide
CAS	139756-02-8
EINECS(EC#)	604-160-8
Molecular Formula	C8H14N4O
MDL Number	MFCD03458971
Molecular Weight	182.22
MOL File	139756-02-8.mol

Synonyms

1-METHYL-3-PROPYL-4-AMINOPYRAZOLE-5-CARBOXAIMDE 4-AMINO-1-METHYL-3-N-PROPYL-1H-PYRAZOLE-5-CARBOXAMIDE 4-AMINO-1-METHYL-3-N-PROPYL-5-PYRAZOLECARBOXAMIDE 4-AMINO-1-METHYL-3-N-PROPYL PYRAZOLE-5-CARBOXAMIDE 4-AMINO-1-METHYL-3-N-PROPYL PYRAZOLO-5-CARBOXAMIDE 4-AMINO-1-METHYL-3-N-PROPYPRZOLE-5-CARBOXAMIDE 4-AMINO-1-METHYL-3-PROPYL-1H-PYRAZOLE-5-CARBOXAMIDE 4-amino-1-methyl-3-propyl-5-pyrazolecarboxamide 4-AMINO-1-METHYL-3-PROPYL PYRAZOLE-5-CARBOXAMIDE 4-Amino-2-methyl-5-propyl-2H-pyrazole-3-carboxamide 4-AMINO-2-METHYL-5-PROPYL-2H-PYRAZOLE-3-CARBOXYLIC ACID AMIDE VIAGRA INTERMEDIATE 1H-Pyrazole-5-carboxamide,4-amino-1-methyl-3-n-propyl 4-AMINO-1-METHYL-3-N-PROPYL-5-PYRAZOLECA 1H-Pyrazole-5-carboxamide,4-am 4-Amino-1-methyl-3-propyl-5-pyrazolecarboxam 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide HCl

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
Usage	A potent hypolipidemic agent. A possible inhibitor of phosphodiesterase 1
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 Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319-H335
Precautionary statements	P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
WGK Germany	3
HS Code	2933.19.4300
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Hazard Information

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

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