Downstream synthetic route of 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

To a mixture of 2-chloropyrimidine-5-boronic acid (32 mg, 0.2 mmol) and N-methyl-N-tetrahydro-2H-pyran-4-ylamine (26 mu, 0.21 mmol) in EtOH (2 mL) was added triethylamine (0.070 mL, 0.5 mmol). The resulting mixture was stirred at 75 C for 5 h. Solvents were removed to give crude (2-(methyl(tetrahydro-2H-pyran-4- yl)amino)pyrimidin-5-yl)boronic acid as a light yellow solid. LCMS [M + H] 238.2. The title compound (white solid, 5.4 mg, 9%) was prepared similar to Example 29 using crude (2-(methyl(tetrahydro-2H-pyran-4-yl)amino)pyrimidin-5-yl)boronic acid (0.2 mmol) and (S)-N-(5-bromo-2-(3,4-dimethylpiperazin-l-yl)-4-fluorophenyl)-6-oxo- 4-(trifluoromethyl)-l,6-dihydropyridine-3-carboxamide (49.1 mg, 0.1 mmol). ‘H NMR (500MHz, CHLOROFORM-d) delta = 8.73 (br s, 1H), 8.57 (s, 2H), 8.52 – 8.40 (m, 1H), 7.87 (br s, 1H), 7.11 – 6.91 (m, 2H), 4.98 (br t, J=11.9 Hz, 1H), 4.11 (br dd, J=4.0, 11.4 Hz, 2H), 3.61 (br t, J=11.6 Hz, 2H), 3.11 (s, 3H), 3.05 – 2.82 (m, 4H), 2.70 – 2.55 (m, 1H), 2.38 (br s, 3H), 2.30 – 2.16 (m, 1H), 1.94 (dq, J=4.4, 12.2 Hz, 2H), 1.70 (br d, J=11.5 Hz, 2H), 1.13 (br s, 3H); LCMS [M + H]+ 604.5., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
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