Application of 863548-52-1,Some common heterocyclic compound, 863548-52-1, name is (1-Methyl-1H-pyrazol-5-yl)methanamine, molecular formula is C5H9N3, 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.
1 1 8 Synthesis of Compound 8 (Formula 7^/Example 1; The lithium salt of 3-cyclobutyl-2,3,4,5-tetrahydro-lH-benzo[d]azepine-7-carboxyhc acid (7)( 0.502g, 2mmol) was stirred in thionyl chloride (7.3OmL, lOOmmol) for 60 minutes and then concentrated in vacuo and azeotroped with toluene to give the acid chloride as a brown solid This material was suspended in dichloromethane (1OmL) and to this was added C-(2-methyl-2H-pyrazol-3-yl)-methylamine (0 22g, 2mmol) and triethylamine (0.28mL, 8mmol) and the reaction stirred for 18 hours. The reaction mixture was concentrated in vacuo and loaded onto an SCX-2 cartridge (2Og) eluting firstly with methanol (1OmL x3) and then 2M ammonia/methanol. Fractions corresponding to the product were combined and concentrated in vacuo and then purified by silica chromatography using methanol/dichloromethane mixtures with added ammonia to give 3-cyclobutyl-N-(( 1 -methyl- 1 H-pyrazol-5-yl)methyl)-2,3 ,4,5-tetrahydro- 1 H-benzo[d]azepine-7- carboxamide (8) in 0.9mmol.1H NMR (400 MHz, DMSO-Cl6): delta 8.80 – 8.91 (m, IH), 7.57 – 7.66 (m, 2H), 7.26 – 7.33 (m, IH), 7.16 – 7.23 (m, IH), 6.11 – 6.18 (m, IH), 4.45 – 4.53 (m, 2H), 3.81 (s, 3H), 2.81 – 2.94 (m, 4H), 2.69 – 2.80 (m, IH), 2.34 (br. s., 4H), 1.95 – 2.06 (m, 2H), 1.71 – 1.84 (m, 2H), 1.49 – 1.65 (m, 2H)
The synthetic route of 863548-52-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED.; POONI, Parminder, Kaur; MERCHANT, Kevin, John; KERR, Catrina; CROSBY, Stuart, Richard; OKAWA, Tomohiro; SASAKI, Mitsuru; GOTOU, Mika; SHOWELL, Graham, Andrew; TEALL, Martin, Richard; WO2010/7382; (2010); A1;,
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