Electric Literature of 2002-04-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, molecular formula is C7H6N4S, molecular weight is 178.21, as common compound, the synthetic route is as follows.
Oxalyl chloride (0.1 rriL, 1.18 mmol, 4.0 eq.) was added to a solution of 4-(benzyloxy)-3- (2-methoxyethoxy)benzoic acid (0.1 g, 0.33 mmol, 1.15 eq.) in dichloromethane (2 rriL) followed by N,N-dimethylformamide (2 drops). The reaction was stirred at room temperature ovemight and the solvent was removed in vacuo. A suspension of 5- (pyrimidin-4-yl)-l,3,4-thiadiazol-2-amine (0.051 g, 0.29 mmol, 1 eq.) in pyridine (1.5 mL) was added and the reaction stirred at ambient temperature overnight. The resultant solid was collected by filtration and washed successively with pyridine (0.5 mL), water, saturated sodium bicarbonate solution and water and then dried in vacuo to afford 4- phenoxy-N-(5-(pyridin-4-yl)-l ,3,4-thiadiazol-2-yl)benzamide as a white solid (0.026 g, 13% yield). NMR (400 MHz, DMSO) 13.19 (1H, s), 8.75 (2H, d, J=6.1 Hz), 7.97 – 7.94 (2H, m), 7.85 (1H, d, J=2.1 Hz), 7.80 (1H, dd, J=2.1 , 8.5 Hz), 7.48 (2H, d, J=7.0 Hz), 7.41 (2H, dd, J=7.3, 7.3 Hz), 7.37 – 7.33 (1H, m), 7.24 (1H, d, J=8.7 Hz), 5.25 (2H, s), 4.27 – 4.23 (2H, m), 3.75 – 3.71 (2H, m), 3.34 (3H, s); MS (ESI+) 463.
The chemical industry reduces the impact on the environment during synthesis 2002-04-2, I believe this compound will play a more active role in future production and life.
Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem