New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1455-77-2
Example 9A(rac)-2-Amino-7-[4-cyano-2-(methylsulfonyl)phenyl]-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]-pyrimidine-6-carbonitrileUnder argon, 4-(2-cyano-3-oxobut-1-en-1-yl)-3-(methylsulfonyflbenzonitrile (1.0 g, 3.65 mmol), 3,5-diaminotriazole (1.08 g, 10.94 mmol, 3.0 eq.), D,L-proline (214 mg, 2.55 mmol, 0.7 eq.) and molecular sieve (4 A, 0.5 g) were suspended in a mixture of pyridine (20 ml) and DMF (30 ml) and stirred for 3 d.More 3,5-diaminotriazole (361 mg, 3.64 mmol, 1 eq.) was added, and the mixture was stirred for a further 5 d.The reaction mixture was then filtered and the filtrate was concentrated under reduced pressure (intermediate 4-[2-cyano-1-(3,5-diamino-1H-1,2,4-triazol-1-yl)-3-oxobutyl]-3-(methylsulfonyl)benzonitrile).Toluene (68 ml), pyridine (55 ml) and 4-toluenesulfonic acid monohydrate (100 mg, 0.53 mmol, 0.14 eq.) were added to the intermediate, and the mixture was heated under reflux (1 h).The reaction mixture was then concentrated under reduced pressure and the residue was dried under high vacuum.Ethanol (30 ml) was added, the residue was suspended and stirred in an ultrasonic bath and the solid was then filtered off and finally dried under high vacuum.This gave 673 mg (50percent of theory) of the title compound.LC-MS (Method 7): Rt=1.00 min; MS (ESIpos): m/z (percent)=356.1 (100) [M+H]+; MS (ESIneg): m/z (percent)=354.2 (100) [M-H]-.1H-NMR (400 MHz, DMSO-d6): delta=2.15 (s, 3H), 3.55 (s, 3H), 5.40 (m, 2H), 7.05 (s, 1H), 7.75 (m, 1H), 8.25 (m, 1H), 8.35 (s, 1H), 11.05 (s, 1H).
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 3,5-Diamino-1,2,4-triazole, in my other articles.
Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2012/4203; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics