Application of 1227594-89-9 ,Some common heterocyclic compound, 1227594-89-9, molecular formula is C6H3F4NO, 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.
[00542] Step C: tert-butyl ethyl(1-((1r,4r)-4-hydroxycyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (30 mg, 0.07 mmol) was dissolved in THF (0.5 mL). 6-hydroxy-2-methylpyridazin-3(2H)-one (26 mg, 0.21 mmol) and PPh3 (55 mg, 0.21 mmol) were added, followed by DIAD (0.041 mL, 0.21 mmol). The reaction mixture was stirred overnight and then concentrated. The residue was dissolved in DCM (1 mL) and 4N HCl in dioxane (1 mL) was added and stirred for 2 h. The reaction mixture was concentrated and the residue purified on C-18 silica column (5 to 95% ACN in water with 0.1% TFA) to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(oxazol-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (17.2 mg, 20% yield). Mass spectrum (apci) m/z = 436.2 (M+H).1H NMR (CD3OD) delta 9.05 (s, 1H), 8.15 (s, 1H), 7.47 (s, 1H), 7.28 (d, J = 9.6 Hz, 1H), 7.00 (d, J = 9.6 Hz, 1H), 6.97 (s, 1H), 5.16 (m, 1H), 4.75 (m, 1H), 3.65 (s, 3H), 3.45 (q, J = 7.2 Hz, 2H), 2.50-2.31 (m, 4H), 1.99-1.86 (m, 4H), 1.38 (t, J = 7.2 Hz, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227594-89-9, its application will become more common.
Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Pyridine – Wikipedia,
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