Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-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 13526-66-4, Safety of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

General procedure: Example 15-5 General procedure for the synthesis of 3-bromo-6-R1-imidazo[1,2-b]pyridazine 4*. (R1= aminyl) by amine (R1H) displacement A mixture of 3-bromo-6-chloroimadazo[1,2-b]pyridazine 2*a (15 g, 64.52 mmol, 1 eq.), the appropriate amine (R1H, 96.78 mmol, 1.5 eq.) and DIPEA (16.90 ml, 96.78 mmol, 1.5eq.) in ethanol (15 ml) was placed in the CEM Microwave and stirred and heated at 160 C for 10 minutes and 180 C for 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water (twice) and brine and then filtered through a pad of silica and washed with ethyl acetate. The organic solvent was evaporated under reduced pressure and the crude residue was slurried in hexane/10% ether. The crystalline product was filtered and washed with hexane/ 10% ether and dried to give the intermediate 3-bromo-6-R1-imidazo[1,2-b]pyridazine 4*.

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; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 821-10-3, 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. 821-10-3, name is 1,4-Dichlorobut-2-yne belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketosulfones 1a-p (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at 25 C. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc15/1e8/1) afforded 4a-p.

The synthetic route of 1,4-Dichlorobut-2-yne has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, belongs to chlorides-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 174913-12-3, COA of Formula: C7H6BrClO

steps 1 and 2-A solution of 1-bromo-3-chloro-5-fluoro-benzene (42a, 55 g, 263 mmol) was cooled to 0 C. and treated with a 25% methanolic sodium methoxide solution (68 mL, 315 mmol) and heated to 40 C. for 3 h. The solution was cooled and partitioned between water (1 L) and a 1:1 mixture of hexane/diethyl ether (3¡Á200 mL). The combined extracts were washed with brine (60 mL), dried (Na2SO4), filtered and the solvents evaporated in vacuo to afford 42b as an oil (57.3 g, 92% pure, 238 mmol). The ether 42b (43 g, 173 mmol) was treated with glacial HOAc (150 mL) and 48% aqueous HBr (100 mL) and heated to 120 C. After 40 h, the volatiles were removed while heated to 80 C. and then cooled to RT. The residue was partitioned between water (100 mL) and DCM (3¡Á250 mL). The combined extracts were washed with H2O (50 mL), aqueous NaHCO3 solution (2¡Á50 mL), brine (50 mL), and (MgSO4). The solvents were removed to afford 23.3 g of 42c as a grey solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-3-chloro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 174913-12-3,Some common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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.

A solution of 1-bromo-3-chloro-5-methoxybenzene (50.0 g, 226 mmol) in dichloromethane (200 mL) was treated with boron tribromide (226 mL, 226 mmol, 1.0 M solution in dichloromethane) and the mixture stirred for 4 h at rt. Additional boron tribromide (678 mL, 678 mmol, 1.0 M solution in dichloromethane) was added and the reaction stirred overnight. The mixture was quenched with water, and the organic phase separated and concentrated to dryness. The residue was dissolved in hexanes and extracted with 1.0 N sodium hydroxide. The aqueous layer was isolated, acidified with 1.0 N hydrochloric acid and extracted with ethyl acetate. The organic layer was isolated, washed with brine, dried over magnesium sulfate, filtered and concentrated to give 43 g of the title compound. 1H NMR (DMSO-c/6) delta 10.36 (s, 1 H), 7.01 – 7.10 (m, 1 H), 6.86 – 6.94 (m, 1 H), 6.75 – 6.84 (m, 1 H).

The synthetic route of 174913-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 7051-16-3, A common heterocyclic compound, 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, molecular formula is C8H9ClO2, 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.

1.0 M solution of boron tribromide in DCM (12.00 mL, 11.49 mmol) was slowly added to a solution of 5-chloro-1,3-dimethoxybenzene 28 (1.00 g, 5.74 mmol) in DCM (10.00 mL) at -78 C. After reaction was allowed to gradually warm to room temperature, the mixture was stirred for 2 days until no starting material was observed by TLC. Reaction mixture was diluted with NaHCO3 (aq. sat.) (50.00 mL) and reaction product was extracted with DCM (3 x 50.00 mL). The combined organic extract was washed with NaCl(sat. aq.) (20.00 mL), dried over anhydrous Na2SO4, and filtered. Obtained supernatant was concentrated under reduced pressure and crude residue was purified by flash column chromatography using n-hexane/ethyl acetate (7:3) to give 5-chlororesorcinol 28b (0.80 g, 96%) as a brown residue. 1H NMR (400 MHz, CDCl3-d) deltaH 6.21 (s, 1H, ArH), 6.37 (d, 2H, J = 2.2 Hz, ArH).

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:
Article; Hossain, Mohammad Anwar; Sattenapally, Narsimha; Parikh, Hardik I.; Li, Wei; Rumbaugh, Kendra P.; German, Nadezhda A.; European Journal of Medicinal Chemistry; vol. 185; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, belongs to chlorides-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 63624-28-2, Application In Synthesis of 2,4-Dimethoxybenzene-1-sulfonyl chloride

1.5 (¡À)-5-Cyano-1-[(2,4-dimethoxyphenyl)sulfonyl]-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate 24.47 mg (0.22 mmol) of potassium tert-butoxide were added undiluted to a solution of 100 mg (0.20 mmol) of (¡À)-5-cyano-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate in 2 ml of absolute dimethylformamide while cooling at 0 C. The reaction mixture was stirred at 0 C. for one hour. A clear colorless solution formed. At 0 C., 51.6 mg (0.22 mmol) of 2,4-dimethoxybenzenesulfonyl chloride were added. The reaction mixture was allowed to thaw to room temperature and was stirred at room temperature overnight. After conversion was complete, the reaction mixture was poured into 10 ml of ice-water and initially neutralized and then adjusted to pH 9 with 2 ml of 1 N sodium hydroxide solution. A precipitate separated out and was washed with water and dried in a vacuum drying oven to result in 68 mg of dry solid. In order to remove the slight impurities, the solid was stirred in 3 ml of diethyl ether. After leaving to stand overnight, the solid was again filtered off and washed with a little diethyl ether and dried. 40 mg (0.06 mmol, 29%) of (¡À)-5-cyano-1-[(2,4-dimethoxyphenyl)sulfonyl]-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate were obtained. ESI-MS [M+H+]=705.4 calculated for C35H40N6O8S=704.81 1H-NMR ([d6]-DMSO, 500 MHz) delta[ppm]=8.22-8.10 (m, 2H), 7.96 (d, 1H, J=8.0 Hz), 7.92 (d, 1H, J=8.3 Hz), 7.85 (d, 1H, J=8.7 Hz), 7.65 (s, 1H), 7.13 (m, 1H), 6.67-6.63 (m, 2H), 4.08 (m, 2H), 3.84 (s, 3H), 3.67-3.45 (m, 3H), 3.51 (s, 3H), 3.04 (m, 2H), 2.74 (pd, 2H, J=9.4 Hz), 2.46 (m, 1H), 2.28 (m, 2H), 2.14 (m, 1H), 2.10 (s, 3H), 1.79 (pt, 2H, J=10.3 Hz), 1.61 (pd, 2H, J=10.2 Hz), 1.36 (m, 2H), 0.99 (t, 3H, J=6.4 Hz).

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; Abott GmbH & Co KG; US2011/65720; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4152-90-3, 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. 4152-90-3, name is (3-Chlorophenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 250 mL round bottom flask equipped with a stir bar was added 4-chloro-3-[(2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)-amino]-benzoic acid (4.8 g, 12.3 mmol), DMF (50 mL), triethylamine (8.3 mL, 60.0 mmol), 3-chlorobenyzl amine (2.2 mL, 18.0 mmol) and then HATU (6.84 g, 18.0 mmol). The reaction was allowed to stir at room temperature for 12 hours, after which it was diluted with ethyl acetate, filtered and then successively rinsed with water and ethyl acetate. The collected solid was dried in an vacuum oven (70¡ã C.) overnight to provide 2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid [2-chloro-5-(3-chloro-benzylcarbamoyl)-phenyl]amide. (Yield 5.5 g, 87percent).HR-MS (ES+) m/z Calculated for C23H18Cl2N5O3S ([M+H]+): 514.0502. Found: 514.0503.

The synthetic route of (3-Chlorophenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1207625-18-0, A common heterocyclic compound, 1207625-18-0, name is 3-Chloro-7H-pyrrolo[2,3-c]pyridazine, molecular formula is C6H4ClN3, 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.

[D] B-bromo-3-chloro-7H-pyrrolo [2 3-c] pyridazine[0253][0254]To a stirred solution of 3-chloro-7H-pyrrolo [2 3-c] pyridazine (1.9 g 12.4 mmol) in DMF (15 mL) was added NBS (2.2 g 13 mmol) and the resulting reaction mixture was stirred at 30for 2 h. After cooling to room temperature the reaction mixture was diluted with water and extrated with EtOAc (20 mL three times) . The combined organics were washed with brine dried over anhydrous Na2SO4 filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (petroleum etherEtOAc 201 to 41) to afford the title compound (1.9 g 65.9yield) as a light yellow solid MS 234.1 [M+H]+.

The synthetic route of 1207625-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; CUMMING, John Graham; LIU, Yongfu; WU, Jun; WANG, Lisha; SHEN, Hong; SHI, Tianlai; (90 pag.)WO2017/133665; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 84859-27-8, name is 5-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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. Product Details of 84859-27-8

Step 3: 6-Chloro-2-(4-diethoxymethyl-pyridin-3-yl)-1-methyl-1 H-benzoimidazole (37c)A solution of 5-chloro-N1-methylbenzene-1,2-diamine (383 mg, 2.446 mmol) and 4- diethoxymethyl-pyrid’ine-3-carbaldehyde (512 mg, 2.446 mmol) in 1 ,4-dioxane (20 mL) was heated to 75 C overnight. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel flash chromatography employing heptane-ethyl acetate (1:1) to give of 6-chloro-2-(4-diethoxymethyl-pyridin-3-yl)-1 -methyl- 1H- benzoimidazole.MS (ESI) m/z 346.0 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84859-27-8, its application will become more common.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 139512-70-2,Some common heterocyclic compound, 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, molecular formula is C6H6ClFN2, 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.

To a mixture of N-[(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)acetyl]-N-methylglycine (150 mg), 4-chloro-5-fluorobenzene-1,2-diamine (81 mg), and DMF (5 mL) were added HOBt (77 mg) and WSC.HCl (107 mg), followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc, and washed with water, a saturated aqueous NaHCO3 solution, and brine in this order, dried over Na2SO4, and then concentrated under reduced pressure. To the residue was added acetic acid (5 mL), followed by heating and stirring at 110 C. for 5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with EtOAc. The organic layer was washed with a saturated aqueous NaHCO3 solution and brine in this order, dried over Na2SO4, and then concentrated under reduced pressure. The obtained solid was washed with EtOAc and then with MeOH, and suspended in MeOH (3 mL). 4 M hydrogen chloride/EtOAc (120 muL) was added thereto, followed by stirring at room temperature for 1 hour. The resulting solid was collected by filtration and then washed with MeOH to obtain N-[(6-chloro-5-fluoro-1H-benzimidazol-2-yl)methyl]-2-(5-chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)-N-methylacetamide hydrochloride (146 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-5-fluorobenzene-1,2-diamine, its application will become more common.

Reference:
Patent; ASTELLAS PHARMA INC.; Shiraki, Ryota; Tobe, Takahiko; Kawakami, Shimpei; Moritomo, Hiroyuki; Ohmiya, Makoto; US2014/315963; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics