Application of 591769-05-0,Some common heterocyclic compound, 591769-05-0, name is 3-Cyclopentylacrylonitrile, molecular formula is C8H11N, 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.
To a solution of 4-(lH-pyrazol-4-yl)pynOlo[l,2-b]pyridazine-3-carbonitrile 16a (60 mg, 0.287 mmol) in DMF (1.5 mL) was added 3-cyclopentylacrylonitrile (109 mg, 0.717 mmol), 2,3,4,6,7,8,9, 10-octahydropyrimido[l,2-a]azepine (0.270 mL, 1.772 mmol) and heated with stirring at 50 °C for 3 h. The reaction mixture was cooled to RT and concentrated in vacuum to dryness. The residue obtained was purified by combiflash column chromatography [silica gel, 4 g eluting with hexanes/ethyl acetate (1 :0 to 2:1)] to give 4-(l-(2-cyano-l-cyclopentylethyl)-lH- pyrazol-4-yl)pyrrolo[l,2-b]pyridazine-3-carbonitrile 16b (56 mg, 59percent, Rf = 0.42 with hexanes/ethyl acetate = 2:1) as a yellow solid; 1H NMR (300 MHz, OMSO-d6) delta 8.80 (d, J= 0.6 Hz, 1H), 8.48 (s, 1H), 8.31 (s, 1H), 8.19 (t, J= 2.1 Hz, 1H), 7.13 (d, J= 2.0 Hz, 2H), 4.64 (td, J = 9.0, 4.8 Hz, 1H), 3.29 – 3.21 (m, 2H), 2.48 – 2.37 (m, 1H), 1.91 – 1.11 (m, 8H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Cyclopentylacrylonitrile, its application will become more common.
Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; WU, Minwan; WO2011/150356; (2011); A1;,
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