Synthetic Route of 16879-39-3 ,Some common heterocyclic compound, 16879-39-3, molecular formula is C6H7BrN2, 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.
Copper (I) iodide (1.013 mg, 5.32 muetaiotaomicron) was added to a mixture of 2- chloropyridine 99% (6.50 mu, 0.069 mmol), N-(4-fluoro-5-(l,2,3,6-tetrahydropyridin- 4-yl)-2-((3S,5R)-3,4,54rimethylpiperazin-1-yl)phenyl)-6-oxo-4-(trifluoromethyl)-l,6- dihydropyridine-3-carboxamide (27 mg, 0.053 mmol) and N,N-diisopropylethylamine (0.028 ml, 0.160 mmol) in ethylene glycol (1.5 ml). The mixture was heated in a microwave reactor at 180 C for lh. The mixture was quenched and worked up in a similar manner to Example 148 to provide the title compound as a yellow powder (8.5 mg, 26 %). 11H NMR (500MHz, METHANOL-d4) delta = 7.99 (dd, J=1.2, 4.9 Hz, 1H), 7.85 – 7.82 (m, 1H), 7.73 – 7.67 (m, 1H), 7.51 – 7.45 (m, 1H), 6.87 – 6.83 (m, 1H), 6.82 – 6.79 (m, 1H), 6.76 – 6.71 (m, 1H), 6.60 – 6.52 (m, 1H), 6.08 – 6.01 (m, 1H), 4.04 – 3.99 (m, 2H), 3.75 – 3.70 (m, 2H), 2.95 – 2.90 (m, 2H), 2.55 – 2.43 (m, 6H), 2.29 – 2.27 (m, 3H), 1.06 (d, J=5.9 Hz, 6H); LCMS [M+H]+ 585.5. A procedure similar to that of Example 270 using N-(4-fluoro-5-(l, 2,3,6- tetrahydropyridin-4-yl)-2-((3S,5R)-3,4,5-trimethylpiperazin-l-yl)phenyl)-6-oxo-4- (trifluoromethyl)-l,6-dihydropyridine-3-carboxarnide (30 mg, 0.059 mmol) and 2-bromo- 4,6-dimethylpyrimidine (13.27 mg, 0.071 mmol) gave the title compound (28 mg, 73 % yield). NMR (500MHz, METHANOL-d4) delta = 7.99 – 7.92 (m, 1H), 7.83 – 7.75 (m, 1H), 6.98 – 6.94 (m, 1H), 6.93 – 6.90 (m, 1H), 6.46 – 6.39 (m, 1H),6.16 – 6.08 (m, 1H), 4.41 – 4.37 (m, 2H), 4.09 – 4.03 (m, 2H), 3.07 – 3.00 (m, 2H), 2.63 – 2.52 (m, 6H), 2.39 – 2.37 (m, 3H), 2.33 – 2.30 (m, 6H), 1.17(d, J=6.0 Hz, 6H); LCMS [M+H]+ 614.7.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16879-39-3, its application will become more common.
Reference:
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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