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| | 4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide Basic information |
| | 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) |
| 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 |
| | 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 |
| | 4-Amino-1-methyl-3-propyl-5-pyrazolecarboxamide Preparation Products And Raw materials |
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