| Identification | More | [Name]
4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide | [CAS]
139756-02-8 | [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 | [EINECS(EC#)]
604-160-8 | [Molecular Formula]
C8H14N4O | [MDL Number]
MFCD03458971 | [Molecular Weight]
182.22 | [MOL File]
139756-02-8.mol |
| Chemical Properties | Back Directory | [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 | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
2933.19.4300 |
| Hazard Information | Back Directory | [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]
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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