Related Products of 762240-92-6,Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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.
Example 1: Preparation of tert-butyl (R)-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-alpha]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)-4-oxobutan-2-ylcarbamate (Compound of formula 2 wherein R is Boc) [35] (R)-3-Boc-amino-4-(2,4,5-trifluorophenyl)-butanoic acid (3.0g, 9.0mmol) and tetrahydrofuran (THF, 30ml) were charged and dissolved in a dry flask, and N-methylmorpholine (2.97ml, 27.0mmol) was added thereto. Then, the mixture was cooled to a temperature of 0 to 5C, and 2-chloro-4,6-dimethoxy-1,3,5-triazine (2.05g, 11.7mmol) was added thereto. After being stirred at a temperature of 0 to 5C for one hour, 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-alpha]pyrazine hydrochloride (2.47g, 10.8mmol) was added and the reaction mixture was stirred while elevating to a temperature of 20 to 25C. After the completion of the reaction was confirmed by TLC, the reaction liquid was cooled to 10C, and dichloromethane (30.0ml) and water (30.0ml) were added thereto, followed by separation of layers. The organic layer was washed with saturated sodium bicarbonate (30.0ml) and saline (30.0ml), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then crystallized from ethyl acetate (12.0ml) and isopropyl alcohol (6.0ml) to afford 4.29g (yield: 94.0%) of tert-butyl (R)-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-alpha]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)-4-oxobutan-2-ylcarbamate.[36] 1H NMR delta 7.04(dd, 1H, J=0.012), 6.84(dd, 1H, J=0.013), 5.01(s, 2H), 4.90(NH), 4.20(s, 2H), 4.10(t, 2H), 4.04(t, 2H), 3.97(m, 1H), 2.97(t, 2H), 2.70(t, 2H),[37] mp: 183.0 to 183.5C (as measured using a capillary melting point apparatus Mettler FP90 at an elevation rate of 2C/min)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, its application will become more common.
Reference:
Patent; ST PHARM CO., LTD.; LIM, Geun Gho; CHANG, Sun Ki; BYEON, Chang Ho; WO2012/99381; (2012); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem