| Identification | Back Directory | [Name]
1-METHYL-1H-PYRAZOL-4-YLAMINE | [CAS]
69843-13-6 | [Synonyms]
69843-13-6
AKOS B022860
AKOS PAO-0224
TIMTEC-BB SBB009607
ART-CHEM-BB B022860
1-methylpyrazol-4-amine
ASINEX-REAG BAS 13529566
4-Amino-1-methylpyrazole
1-Methyl-4-amino-pyrazole
1-METHYL-1H-PYRAZOL-4-YLAMINE
1-Methyl-1H-pyrazole-4-ylaMine
1-Methyl-4-AMinoMethy pyrazole
1-methyl-1H-pyrazol-4-amine hydrochloride
1-methyl-1H-pyrazol-4-amine(SALTDATA: 1.15HCl) | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C4H7N3 | [MDL Number]
MFCD05667135 | [MOL File]
69843-13-6.mol | [Molecular Weight]
97.12 |
| Chemical Properties | Back Directory | [Melting point ]
47-50℃ | [density ]
1.141 g/mL at 25 °C | [refractive index ]
n20/D1.556 | [Fp ]
>110 °C | [storage temp. ]
?20°C | [form ]
liquid | [pka]
3.70±0.10(Predicted) | [color ]
Pale red | [Sensitive ]
Air Sensitive | [Boiling point ]
45-80°C/760 mmHg | [InChI]
InChI=1S/C4H7N3/c1-7-3-4(5)2-6-7/h2-3H,5H2,1H3 | [InChIKey]
HEFHQCFTJGKPMD-UHFFFAOYSA-N | [SMILES]
N1(C)C=C(N)C=N1 | [CAS DataBase Reference]
69843-13-6 |
| Hazard Information | Back Directory | [Synthesis]
1-Methyl-4-nitro-1H-pyrazole (1.62 g, 12.7 mmol) was used as the raw material, which was dissolved in methanol (250 mL) and hydrogenated on an H-Cube reactor at 60 bar hydrogen pressure and 70 °C to obtain 1-methyl-1H-pyrazol-4-amine (1.23 g, 99% yield). Subsequently, 1-methyl-1H-pyrazol-4-amine (700 mg, 7.0 mmol), 3-amino-6-bromopyridinecarboxylic acid (1.86 g, 8.5 mmol), PyBop (4.12 g, 8.0 mmol), dichloromethane (30 mL), and diisopropylethylamine (3.8 mL) were added to a 100 mL round-bottomed flask and the reaction mixture was stirred at room temperature for 24 h. The reaction progress was monitored by LCMS. Upon completion of the reaction, the solvent was removed by distillation and the crude product was purified by fast chromatography (eluent: heptane/ethyl acetate). A portion of the product was further purified by reversed-phase HPLC to afford the target compound 317.The product characterization data were as follows:1H NMR (400 MHz, DMSO) δ 10.25 (s, 1H), 8.03 (s, 1H), 7.70 (s, 1H), 7.43 (d, J = 8.7 Hz, 1H), 7.19 (d, J = 8.7 Hz, 1H), 7.02 (br, 2H), 3.81 (s, 3H); MS (ESI) m/z: 296.0/298.0 [M + H]+. | [References]
[1] Patent: US2011/251176, 2011, A1. Location in patent: Page/Page column 160-161
[2] Patent: WO2015/25197, 2015, A1. Location in patent: Paragraph 00077
[3] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0179; 0181
[4] Patent: CN106432246, 2017, A. Location in patent: Paragraph 0453; 0806; 0807; 0808
[5] Patent: WO2015/161830, 2015, A1. Location in patent: Paragraph 00770 |
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