Category: 70894-71-2

Synthetic Route of 70894-71-2, A common heterocyclic compound, 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine, molecular formula is C11H15NO, 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.

6-Chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile To a stirred solution of 6,8-dichloroimidazo[1,2-b]pyridazine-3-carbonitrile and 8-bromo-6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile (15 g, 71.09 mmol) in THF (20 mL) was added DIPEA (14 mL, 78.19 mmol) at room temperature under argon atmosphere, prior to the addition of N-(4-methoxybenzyl)cyclopropanamine (13.99 g, 78.19 mmol) at room temperature. The reaction mixture was stirred for 4 h at 65 C. The reaction mixture was quenched with water and extracted with ethyl acetate (2*200 mL). The combined extracts were washed with brine, dried over Na2SO4, concentrated to give the crude product, which was purified on a silica gel column (eluting with 20% ethyl acetate: pet ether) to get the title compound 6-chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile (18 g, 71.1%) as a pale yellow solid. ES+, m/z 354.4 [M+1].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Polaris Pharmaceuticals; WEBBER, Stephen E.; TAO, Xueliang; BRIN, Elena; (85 pag.)US2017/369489; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 70894-71-2, category: ethers-buliding-blocks

General procedure: N-cyclopropyl-N-substituted benzylamine (4.0 mmol) inethanol was mixed with carbon disulfide (4.0 mmol) under ice coldcondition. To the resultant yellow dithiocarbamic acid solution,aqueous solution of NiCl2,6H2O (2.0 mmol) was added with constantstirring. The solid which precipitated was washed severaltimes with cold water and then dried (Fig. 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(4-Methoxybenzyl)cyclopropanamine, and friends who are interested can also refer to it.

Reference:
Article; Sathiyaraj; Srinivasan; Thirumaran; Velmurugan; Journal of Molecular Structure; vol. 1102; (2015); p. 203 – 209;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 70894-71-2, Recommanded Product: 70894-71-2

A solution of ethyl 6,8-dichloroimidazo[l ,2-b]pyridazine-3-carboxylate (4.0 g, 15.38 mmol), N-(4-methoxybenzyl)cyclopropanamine (4.09 g, 23.07 mmol) and diisopropylethyl amine (5.37 mL, 30.8 mmol) in tetrahydrofuran (THF, 5 mL) was refluxed at 70 C overnight. The reaction was concentrated and the crude product was purified using silica gel chromatography (25-30% ethyl acetate: petroleum ether), to provide ethyl 6-chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[l ,2- b]pyridazine-3-carboxylate (4.3 g, 56% yield). 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 8.14 (1 H, s), 7.05 – 7.07 (1 H, m), 7.02 – 7.05 (1 H, m), 6.76 – 6.79 (1 H, m), 6.74 – 6.76 (1 H, m), 6.60 (1 H, s), 5.61 (2 H, s), 4.43 (2 H, q, J=7.22 Hz), 3.75 (3 H, s), 2.45 – 2.54 (1 H, m), 1.41 (3 H, t, J=7.05 Hz), 0.96 – 1.04 (2 H, m), 0.76 – 0.84 (2 H, m). LC retention time 2.22 min [O]. MS (E+) m/z: 401 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of N-(4-Methoxybenzyl)cyclopropanamine

6,8-Dichloroimidazo[l,2-b]pyridazine-3-carboxamide (2.5 g, 10.9 mmol), N-(4- methoxybenzyl)cyclopropanamine (3.36 g, 18.98 mmol) and diisopropylethylamine (4.42 ml, 25.3 mmol) were dissolved in tetrahydrofuran (THF, 100 mL) and then refluxed overnight. The solvent was removed in vacuo and the crude product was taken up in chloroform and purified via chromatography to provide the product (2.6 g, 64% yield). NMR (400 MHz, DMSO-D6) delta ppm 8.10 (1 H, s), 7.96 (2 H, s), 7.11 (2 H, d, J=8.56 Hz), 6.83 (2 H, d, J=8.81 Hz), 6.73 (1 H, s), 5.65 (2 H, s), 3.68 (3 H, s), 2.55 – 2.63 (1 H, m), 0.93 – 1.03 (2 H, m), 0.76 – 0.84 (2 H, m).

The synthetic route of 70894-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem