With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.
EXAMPLE 95 1-[2-(Pyridazin-4-ylamino)-ethyl]-piperazin-2-one. 1-(2-Aminoethyl)-4-(tert-butyloxycarbonyl)-piperazin-2-one from EXAMPLE 92, Part A (1.0 g, 4.1 mmol) is treated with 3,4,5-trichloropyridazine (0.81 g, 4.1 mmol), triethylamine (0.57 ML, 4.1 mmol), THF (25 ML) and heated to 120 C. in a sealed tube for 3 hours.Upon cooling, the solution is diluted with ethyl acetate and washed with aqueous sodium bicarbonate (25 ML), water and dried over sodium sulfate.The organic layer is concentrated and chromatographed (5% methanol/methylene chloride) to give a mixture of isomers (0.8 g, 20 mmol).The mixture is dissolved in 0.5 M sodium methoxide in methanol (200 ML), treated with 10% Pd/C (0.5 g) and agitated under 50 PSI of hydrogen for 20 hours.The reaction mixture is filtered; the filtrate is concentrated to a residue which is chromatographed (NH4OH/H2O/MeOH/EtOAc, 1:1:2:90) to give crude 4-(tert-butyloxycarbonyl)-1-[2-(pyridazin-4-ylamino)-ethyl]-piperazin-2-one.This material is dissolved in a minimal amount of THF and treated with a saturated solution of HCl in ethyl acetate (50 ML).The solution is stirred at ambient temperature for 2 h and diluted with diethyl ether (50 ML).The precipitated title compoundcompound is collected and air dried (0.5 g, 1.7 mmol). MS m/z: 367, [M+1]+; 1H NMR (CD3OD, 300 MHz) delta8.8 (d, 1H), 8.5 (s, 1H), 7.4 (d, 1H), 4.1 (s, 2H), 3.5-3.8 (m, 8H)., 14161-11-6
14161-11-6 3,4,5-Trichloropyridazine 70111, apyridazine compound, is more and more widely used in various.
Reference£º
Patent; AVENTIS PHARMACEUTICALS INC.; US2004/102450; (2004); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem