Application of 49607-51-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 49607-51-4 name is 1-Methyl-1H-1,2,4-triazol-3-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Triphosgene (0.588 g, 1.982 mmol) was added to a stirred solution of (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine (0.5 g, 1.982 mmol) in tetrahydrofuran (20 mL) at 0¡ã C. and stirred for 30 min. Triethylamine (0.829 mL, 5.94 mmol) and 1-methyl-1H-1,2,4-triazol-3-amine (0.486 g, 4.95 mmol) was added at 0¡ã C. The reaction mixture was stirred for 48 h at 70¡ã C. The reaction mixture was cooled to 28¡ã C., and was partitioned between water (50 mL) and DCM (50 mL). The separated organic layer was washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and filtrate was evaporated to afford crude yellow solid (TLC eluent: 10percent MeOH in EtOAc: Rf-0.3; UV active). The crude compound was purified by (100-200 mesh) silica gel and was eluting with 5percent MeOH in ethyl acetate to afford (4S)?N-(1-methyl-1H-1,2,4-triazol-3-yl)-7-(2-methylpyridin-4-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-car-boxamide (0.215 g, 0.563 mmol, 28.4percent yield) as light yellow solid, LCMS (m/z): 377.28 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 13.44 (s, 1H), 8.55 (d, J=5.2 Hz, 1H), 8.36 (s, 1H), 7.96 (s, 1H), 7.86-7.61 (m, 3H), 5.44 (dd, J=5.8, 3.0 Hz, 1H), 3.83 (s, 3H), 3.27 (d, J=30.5 Hz, 3H), 2.95 (dd, J=12.0, 3.2 Hz, 1H), 2.59 (s, 3H), 2.23 (ddt, J=16.9, 9.7, 4.4 Hz, 1H), 1.91 (dt, J=14.7, 7.4 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-1,2,4-triazol-3-amine, and friends who are interested can also refer to it.
Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics