Reference of 33050-36-1, These common heterocyclic compound, 33050-36-1, name is 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, its 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 101-(2-Morpholin-4-ylethyl)-3-[6-([1,2,4]triazolo[4,3-b]pyridazin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]ureaa) The 1-(2-morpholin-4-ylethyl)-3-[6-([1,2,4]triazolo[4,3-b]pyridazin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]urea can be prepared in the following way:277 mg of n-tributyl phosphine are added to a solution of 462 mg of 1-(2-morpholin-4-ylethyl)-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea in 5.5 cm3 of tetrahydrofuran. This mixture is stirred for 1 h at 20 C. with nitrogen sparging, before the addition of 176 mg of 3-chloro-1,2,4-triazolo[4,3-b]pyridazine, 166 mg of potassium tert-butoxide, 12 mg of tetraphenyldiphosphoxane and 11 cm3 of toluene and stirring for 30 min at 20 C. with nitrogen sparging. 10 mg of tris(1,5-diphenylpenta-1,4-dien-3-one)dipalladium(0) are then added to the resulting mixture and the subsequent mixture is brought to reflux for 17 h. The solvent is concentrated under reduced pressure and the residue is then taken up in water and 0.1N hydrochloric acid HCl. The mixture obtained is then extracted with a 90/10 mixture of ethyl acetate/methanol. 632 mg of a yellow oil are obtained, and chromatographed on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 muM), elution being carried out with a gradient of dichloromethane then dichloromethane/methanol: 99/1, 98/2, 97/3, 96/4, 95/6, 92/8, 90/10, 80/20. 75 mg of 1-(2-morpholin-4-ylethyl)-3-[6-([1,2,4]triazolo[4,3-b]pyridazin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]urea are thus obtained in the form of a beige powder, the characteristics of which are as follows:MELTING POINT: 252 C. (Koefler block)NMR SPECTRUM 1H NMR (400 MHz, d6-DMSO) deltappm: 2.36-2.45 (m, 6H) 3.24-3.36 (m, 2H) 3.55-3.63 (m, 1H)6.78 (br. s., 0H) 7.38-7.48 (m, 0H) 7.57 (d, J=8.5 Hz, 0H) 8.04 (d, J=1.5 Hz, 0H) 8.43 (dd, J=9.5,1.5 Hz, 0H) 8.70 (dd, J=4.5, 1.5 Hz, 0H) 10.85-10.95 (m, 0H)MASS SPECTRUM: UPLC-MS-DAD-ELSD: 457(+)=(M+H)(+).
Statistics shows that 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 33050-36-1.
Reference:
Patent; sanofi-aventis; US2010/298315; (2010); A1;,
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