Electric Literature 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.
[00643] Step C: (1r,4r)-4-(6-(ethylamino)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexan-1-ol (0.0101 g, 0.0296 mmol), 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (0.0161 g, 0.0887 mmol), PPh3 (0.0233 g, 0.0887 mmol) were dissolved in THF (0.5 mL) and then DIAD (0.0179 g, 0.0887 mmol) was added and stirred overnight and then concentrated. The residue was purified over preparative HPLC (5-95% ACN in water with 0.2% TFA) and concentrated to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (5.6 mg, 25.8 % yield). Mass spectrum (apci) m/z = 505.2 (M+H).1H NMR (CD3OD) delta 8.91 (s, 1H), 8.13 (d, 1H), 7.70 (s, 1H), 7.20 (m, 1H), 6.82 (s, 1H), 5.53 (s, 1H), 4.99 (m, 1H), 4.70 (m, 1H), 3.42 (q, J = 7.0 Hz, 2H), 2.61 (s, 3H), 2.53-2.30 (m, 4H), 1.96 (m, 4H), 1.36 (t, J = 7.0 Hz, 3H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.
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,
Pyridine | C5H5N – PubChem