Month: August 2021

Reference of 348-59-4,Some common heterocyclic compound, 348-59-4, name is 2,5-Dichlorofluorobenzene, molecular formula is C6H3Cl2F, 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 19 2-[3-(2,5-Dichloro-phenoxy)4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-19) step 1-To a solution of 12a (0.200 g; 0.960 mmol) and NMP (4 mL) was added K2CO3 (0.398 g; 2.88 mmol) and 1,4-dichloro-2-fluoro-benzene (0.124 mL; 1.056 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was purified by SiO2 chromatography eluding with a gradient of hexane/EtOAc (100:0 to 60:40) to afford 142. steps 2 and 3-Hydrolysis and formation of the acid chloride were carried as described in step 7and 8 of Example 1 and used without additional purification. step 4-The acid chloride from step 3 (0.415 mmol) was dissolved in acetone (2 mL) and the flask and purged with nitrogen. NaHCO3 (0.070 g; 0.83 mmol) was added followed by 4-amino-benzenesulfonamide (0.072 g; 0.415 mmol) and water (4 mL). The mixture was sonicated for 5 min and allowed to stir for 12 h at RT. The reaction mixture was filtered and the crude product was washed sequentially with water and diethyl ether to afford I-19 Compound I-21 was prepared in the same manner except 4-amino-benzenesulfonamide was replaced with 2-chloro-phenylamine.

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

Reference:
Patent; Roche Palo Alto LLC; US2005/239880; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., name: 4-Bromo-2-chloroaniline

a Tert-butyl N-(4-bromo-2-chlorophenyl)carbamate A solution of 4-bromo-2-chloroaniline (5.00 g, 0.0242 mol) in tetrahydrofuran (50 mL) was reacted with a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (53.2 mL, 0.0532 mol). The mixture was stirred 15 minutes at ambient temperature. Di-tert-butyl dicarbonate (6.34 g, 0.0290 mol) was added and the solution was stirred for 2 hours. The solvent was removed in vacuo, and the crude material was purified by flash column chromatography on silica using heptane /ethyl acetate (4:1). The solvent was removed in vacuo to give tert-butyl N-(4-bromo-2-chlorophenyl)carbamate as a white solid (4.214 g, 0.0137 mol). 1H NMR (DMSO-d6, 400 MHz) delta 8.75 (s, 1H), 7.71 (d, 1H), 7.54 (d, 1H), 7.50 (dd, 5H), 1.46 (s, 9H); TLC (heptane/ethylacetate 4:1) Rf 0.54.

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; Abbott Laboratories; US2002/156081; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H6BrClO

To a 5 ml of toluene solution containing 0.20 g of 3 (S) -aminopyrrolidine-1-carboxylic acid tert-butyl ester (1.1 mmol) and 0.238 g of 2-chloro-3-bromoanisole (1.1 mmol) were added 67.0 mg of BINAP (0.11 mmol), 24 mg of tris (dibenzylideneacetone) dipalladium (0.027 mmol) and 144 mg of sodium tert-butoxide (1.5 mmol). The mixture was heated under reflux under a nitrogen atmosphere at 100,C for one hour. After cooling to room temperature, the reaction solution was filtered EPO using Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 10 : 1 ? 3 : 1) . The purified product was concentrated to dryness under reduced pressure to thereby obtain 0.28 g of light yellow amorphous solid 3 (S) – (3-chloro-4-methoxyphenylamino)pyrrolidine-l-carboxylic acid tert-butyl ester. 1H-NMR(CDCl3) deltappm: 1.47(9H,s), 1.80-1.90 (IH,m) , 2.10-2.20 (lH,m) , 3.10-3.25 (IH,m) , 3.38-3.75(3H,m), 3.83(3H,s), 3.92-3.96 (IH,m) , 6.47 (IH,dd, J=2.8Hz, J=8.8Hz), 6.67 (IH, d, J=2.8Hz) , 6.81 (IH, d, J=8.8Hz) .

The synthetic route of 50638-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2006/121218; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 13078-79-0

General procedure: To a solution of amine 12 (Scheme 5, 1.0 equiv) in anhydrous CH2C12 (10 mE) cooled in an ice/water bath were sequentially added triethylamine (1.1 equiv) and then carbon disulfide (1.1 equiv). The solution was stirred for 30 mm at 00 C. Afier this time, methyl iodide (1.2 equiv) was then added and the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was then poured into 1 M H2504 and extracted with EtOAc (3×10 mE). The combined organic solutions were washed with brine, dried over anhydrous Na2504, and concentrated to afford crude material 13 which was purified by chromatography (silica, EtOAc/hexanes). The majority of the dithiocarbamates exist in tautomeric form (25% to 35%) as observed by ?H NMR, and are listed with spectral data.

The synthetic route of 13078-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEWLINK GENETICS CORPORATION; Mautino, Mario; Jaipuri, Firoz; Marcinowicz-Flick, Agnieszka; Kesharwani, Tanay; Waldo, Jesse; (201 pag.)US10047066; (2018); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7ClO2

2-(Methylamino)ethanol (22.0 g, 290 mmol) is added all at once to a stirred solution of 3,4-methylenedioxybenzyl chloride (25.0 g, 147 mmol) in DCM (45 mL) at -78 C. under nitrogen. The solution is stirred for 15 minutes at -78 C. then allowed to warm to room temperature overnight (16 h). The reaction is quenched with 1.2 M NaOH (100 mL), washed twice with water, dried of MgSO4, and filtered. Concentration under reduced pressure afforded 25.3 g (83%) of 2-(benzo[1,3]dioxol-5-ylmethyl-methyl-amino)-ethanol as a clear oil which was suitable for use in the next step.

The synthetic route of 20850-43-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalypsys, Inc.; US2006/116515; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, molecular formula is C8H11Cl2NO, 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. category: chlorides-buliding-blocks

10-[(3-chloro-4-methoxybenzyl)amino]-2-methyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile A mixture of 4 (0.12 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (0.12 mmol), NaI (0.006 mmol), and phenol (0.12 mmol) was heated at 130 C. for 2.5 h. The reaction mixture was diluted with Et2O (10 mL) and washed with 1N NaOH (3*5 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by Flash Chromatography (AcOEt:MeOH 8:2) to give the desired compound B (33% of yield). MS ESI (m/z) 394 (M+H)+, 1H NMR (300 MHz, CDCl3) delta 8.32 (d, 1H, J=1.2 Hz), 7.97 (d, 1H, J=8.7 Hz), 7.71 (dd, 1H, J1=1.8, J2=8.7 Hz), 7.37 (d, 1H, J=2.1 Hz), 7.18 (dd, 1H, J1=2.4, J2=8.7 Hz), 6.94 (d, 1H, J=8.4 Hz), 4.57 (d, 2H, J=6.0 Hz), 4.11 (br s, 1H), 3.92 (s, 3H), 3.54 (s, 2H), 3.22 (t, 2H, J=6.3 Hz), 2.83 (t, 2H, J=6.3 Hz), 2.52 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41965-95-1, its application will become more common.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 39885-50-2, A common heterocyclic compound, 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, molecular formula is C7H5ClF3N, 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 4Preparation of 2-chloro-6-iodo-4-(trifluoromethyl)benzenamineIodine monochloride (17.2 g, 108 mmol) in hydrochloric acid (36percent, 21.4 g) and water (35 mL) was added dropwise to 2-chloro-4-(trifluoromethyl)benzenamine (20.0 g, 102 mmol) in hydrochloric acid (36percent, 20.7 g) and water (140 mL). The mixture was warmed to 50 0C for a total of 8 h. Sodium hydroxide (50percent, 33.5 g, 419 mmol) was added to the mixture at room temperature. The mixture was extracted with dichloromethane (2 x 250 mL), and the extracts were dried and evaporated to give the product as an oil (31.83 g, 97percent yield). 1H NMR (CDCl3) 7.78 (s, IH), 7.5 (s, IH), 4.87 (br s, 2H).

The synthetic route of 39885-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2009/126668; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 110407-59-5, These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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.

Step E: Preparation of 4-chloro-a-(2-chloro-4-fluorophenyl)-l-(2,6-difluorophenyl)- lH-imidazole-5 -methanol; To a mixture of l-bromo-2-chloro-4-fluorobenzene (0.12 mL, 0.99 mmol) in tetrahydrofuran (5 mL) at about -78 C was added dropwise over 5 minutes n-butyllithium (2.5 M in hexanes, 0.37 mL, 0.94 mmol) while maintaining the temperature of the reaction mixture below -65 C. After the addition was complete, 4-chloro-l-(2,6-difluorophenyl)- lH-imidazole-5-carboxaldehyde (i.e. the product of Step D) in tetrahydrofuran (2 mL) was added dropwise to the reaction mixture while maintaining the reaction mixture at about -62 to -65 C. After 20 minutes, saturated aqueous ammonium chloride solution (5 mL) was added in one portion to the reaction mixture, the mixture was allowed to warm to ambient temperature (about 20 C), and then water (1 mL) was added. The resulting mixture was poured onto a solid phase extraction tube (Varian Chem Elute, prepacked with diatomaceous) and eluted with ethyl acetate (50 mL). The ethyl acetate eluant was concentrated under reduced pressure and the resulting material was triturated with ethyl acetate -hexanes to provide a solid. The solid was recrystallized from ethyl acetate-hexanes to provide the title compound, a compound of the present invention, as a solid (0.080 g). in NMR (DMSO- ): delta 7.71 (m, 1H), 7.45-7.35 (m, 4 H), 7.20 (m, 1H), 6.68 (m, 1H), 6.24 (br s, 1H), 5.71 (s, 1H).

Statistics shows that 2-Chloro-4-fluorobromobenzene is playing an increasingly important role. we look forward to future research findings about 110407-59-5.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; BEREZNAK, James, Francis; KAR, Moumita; TAGGI, Andrew, Edmund; CHEN, Yuzhong; WO2012/44650; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H3BrClF

Step 1 : tert-butyl 4-(2-chloro-4-fluorophenyl)piperazine-l-carboxylate (0979) [00342] To the solution of A18-1 (200 mg, 1 mmol, 1.0 eq), Pd2(dba)3 (44 mg, 48 umol, (0980) 0.05 eq), BINAP (60 mg, 0. 1 mmol, 0. 1 eq), f-BuONa (184 mg, 1.9 mmol, 2.0 eq) in toluene (5 mL) was added fert-butyl piperazine- l-carboxylate (267 mg, 1.4 mmol, 1.5 eq). The mixture was stirred at 1 10 C for 16 hr. The reaction was monitored by TLC. The reaction was concentrated under reduced pressure. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=20: 1) to give the A18-2 (187 mg, 0.6 mmol, 62.2% yield) as a yellow oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 110407-59-5.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; LIN, Tracy Tzu-Ling Tang; KONRADI, Andrei W.; VACCA, Joseph; SHEN, Wang; COBURN, Craig; (231 pag.)WO2017/58716; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 102-49-8, These common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, 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.

Step 4: 1-(3-amino-1H-1,2,4-triazol-5-yl)-N-(3,4-dichlorobenzyl)piperidine-4-carboxamideTo a suspension of 1-(3-amino-1H-1,2,4-triazol-5-yl)piperidine-4-carboxylic acid hydrochloride (200 mg, 0.62 mmol) in CH2Ch(20 ml), DIPEA (0.64 ml, 3.72 mmol) was added. Then sequentially, 0-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium5 hexafluorophosphate (HATU) (130 mg, 0.34 mmol) and 3,4-dichloro-benzylamine (55 mg, 0.31 mmol) were added.Reaction mixture was stirred at room temperature for 20 h. Precipitatewas filtered, washedwith several times with Et20, dissolved in 4M NaOH (20 ml) and extracted with ethyl acetate(5 x 40 ml). Combinedorganic layers were washed withbrine (2 x 20 ml), dried over MgS04 and strippedto give 85 mg of crude product.10 Crystallization with MeOH I AcOEt I Et20 gave 46 mg of pure product(yield 40 percent) 1H NMR (DMSO-d6, 200 MHz) 8 (ppm): 10.95 (bs, 1 H), 8.37 (t, 1=5.6 Hz, 1H), 7.55 (d, 1=8.6 Hz, 1 H), 7.43 (d, 1=1.5 Hz, 1 H), 7.18 (dd, ]]=8.6 Hz, 12=1.5 Hz, 1 H), 5.57 (bs, 1 H), 4.21 (d, 1=5.6 Hz, 2 H), 3.77 (d, 1=13.1 Hz, 2 H), 2.61-2.52 (m, 2 H), 2.35-2.19 (m, 1 H), 1.72-1.41 (m, 4 H). ESI MS for C1sH18ChN60 calculated 368.09, found 369.51371.5 [M+H]+

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE INSTITUTE FOR DRUG DELIVERY; CORMAN, Michael L.; HUNGERFORD, William M.; GOLEBIOWSKI, Adam; BECKETT, Raymond P.; MAZUR, Marzena; OLEJNICZAK, Sylwia; OLCZAK, Jacek; WO2015/95701; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics