Category: 33050-36-1

Application of 33050-36-1, 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. 33050-36-1 name is 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, 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.

3-Mercapto-s-triazolo[4,3-b]pyridazine A mixture of 1.20 g. (8 mmole) of 3-chloro-s-triazolo[4,3-b]pyridazine [P. Francavilla and F. Lauvia, J. Het. Chem., 8, 415 (1971) and 120 g. (16 mmole) of KSH in 20 ml. of ethanol was heated for 8 hours at 130 in a sealed tube. After cooling the mixture was evaporated to dryness and the residue was dissolved in 100 ml. of water, treated with active carbon, acidified to pH 1 with dil. HCl to precipitate 3-mercapto-s-triazolo[4,3-b]pyridazine which was collected, washed with 10 ml. of water and dried in vacuo over P2 O5 to yield 0.75 g. (62%), m.p. 260-270 (dec.). IR: nu maxKBr 3080, 2940, 2760, 1620, 1500, 1280, 1055 cm-1. NMR: ? ppmDMSO-d6 6.99 (1 H, d-d, 4 & 10 Hz, 7-H), 7.67 (1 H, d-d, 2 & 10 Hz, 8-H), 8.15 (1 H, d-d, 2 & 4 Hz, 6-H), 12.3 (1 H, br-s, disappear by addition of D2 O). Anal. Calcd. for C5 H4 N4 S. 1/2H2 O: C, 37.26; H, 3.13; N, 34.76. Found: C, 37.35; H, 2.32; N, 34.81.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Company; US3946000; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics