Application of 100047-56-1, A common heterocyclic compound, 100047-56-1, name is 5-Bromo-3-methylpyrazin-2-ol, molecular formula is C5H5BrN2O, 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.
To a solution of (lR,3s,5S)-tert-butyl 3-((ls,4S)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (100 mg, 0.307 mmol), 5-bromo-3-methylpyrazin-2-ol (69.69 mg, 0.369 mmol), triethylamine (42.83 mu?, 0.307 mmol) and triphenylphosphine (88.65 mg, 0.338 mmol) in THF (2 mL) at ice -water bath under nitrogen was added DIAD (0.123 mL, 0.369 mmol) dropwise. The reaction mixture was slowly warmed to room temperature and stirred overnight, then concentrated. The residue was purified by semi preparative HPLC (35- 95% CH3CN/H20 over 30 min) then neutralized to give the title compound (36 mg, 72.52 muiotaetaomicron?, 23.6% yield) as oil. Exact mass calculated for CzsI^Br^C^: 495.2, found LCMS m/z = 497.6 [M+H]+; ‘H NMR (CDC13 , 400 MHz) delta ppm 1.48 (s, 9H), 1.42-1.65 (m, 8H), 1.82-1.96 (m, 6H), 2.05-2.12 (m, 2H), 2.41 (d, = 0.6 Hz, 3H), 3.42-3.48 (m, 1H), 3.75-3.86 (m, 1H), 4.10- 4.30 (m, 2H), 4.92-5.00 (m, 1H), 7.97 (d, = 0.6 Hz, 1H).
The synthetic route of 100047-56-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem