Application of 571189-49-6 , The common heterocyclic compound, 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, molecular formula is C10H16N4, 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.
Under N2 atmosphere, to a solution of 2′-chloro-2,3,5,6-tetrahydro-8’H-spiro[pyran- 4,9′-pyrazino[r,2′: l,5]pyrrolo[2,3-d]pyrimidine] (32, 50 mg, 0.18 mmol) and 5-(4- methylpiperazin-l-yl)pyridin-2-amine (52 mg, 0.27 mmol) in dioxane (4 mL) was added CS2CO3 (170 mg, 0.52 mmol), Pd(OAc)2 (8 mg, 0.04 mmol) and X-Phos (12 mg, 0.03 mmol). After stirring at 100 C for 12 h, the mixture was directly concentrated in vacuo. The resulting residue was purified by prep TLC to provide N-(5-(4-methylpiperazin-l-yl)pyridin-2-yl)- 2,3,5,6 etrahydro-8H-spiro[pyran-4,9′-pyrazino[l 2^ 1,5]pyiTolo[2,3-d]pyriiTddin]-2′-amine (COMPOUND 10, 20 mg, 0.05 mmol). MS (ESI+): m/z 433 [M + H]+; NMR (300 MHz, MeOD): delta 8.90 (s, 1H), 8.53 (s, 1H), 8.09 (d, J = 9.0 Hz, 1H), 8.03 (d, J = 3.0 Hz, 1H), 7.70 (d, J= 7.2 Hz, 1H), 7.09 (s, 1H), 4.24 (d, J= 1.7 Hz, 2H), 4.01 (dd, J= 12.3, 4.8 Hz, 2H), 3.77 (t, J = 11.8 Hz, 2H), 3.56 – 3.33 (m, 8H), 3.28 – 3.17 (m, 2H), 2.95 (s, 3H), 1.82 (d, J = 13.6 Hz, 2H).
The synthetic route of 571189-49-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copelnad; (156 pag.)WO2018/5863; (2018); A1;,
Pyridine – Wikipedia,
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