Electric Literature of 51105-90-9, These common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Synthesis of methyl 1-((6-cyclopropyl-8-(3-hydroxyoxetan-3-yl)imidazo[1,2-a]pyridin-2-yl)methyl) -1H-pyrazole-4-carboxylate. A mixture of 3-(2-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)oxetan-3-ol (1.2 g, 4.3 mmol), methyl 1H-pyrazole-4-carboxylate (0.54 g, 4.3 mmol) and Cs2CO3 (2.8 g, 8.6 mmol) in DMF (10 mL) was stirred at 50 C. for 3 h. The reaction mixture was filtered through celite, and the filtrate was diluted with H2O (100 mL) and extracted with ethyl acetate (100 mL). The combined organic layers were concentrated to give the crude, which was purified by silica gel column chromatography (DCM/MeOH=6/1) to give methyl 1-((6-cyclopropyl-8-(3-hydroxyoxetan-3-yl)imidazo[1,2-a]pyridin-2-yl)methyl)-1H-pyrazole-4-carboxylate (890 mg, 56% yield) as a yellow solid. ESI-MS [M+H]+: 369.2. 1H NMR (400 MHz, DMSO-d6) delta8.41 (s, 1H), 8.30 (d, J=1.2 Hz, 1H), 7.90 (s, 1H), 7.70 (s, 1H), 6.45 (s, 1H), 5.50 (s, 2H), 5.24 (d, J=6.5 Hz, 2H), 4.66 (d, J=6.5 Hz, 2H), 3.74 (s, 3H), 1.94 (td, J=8.4, 4.2 Hz, 1H), 0.97-0.89 (m, 2H), 0.72-0.65 (m, 2H).
The synthetic route of 51105-90-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
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