Category: chlorides-buliding-blocks

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. 69695-61-0, name is 2-Chloro-4-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-4-(trifluoromethoxy)aniline

General procedure: Under argon condition [26], p-TsCl (p-toluenesulfonyl, 1.2 mmol) in 2 mL dichloromethane was injected to the 2 mL dichloromethane mixture of compounds 1-9 (1 mmol) and 4-dimethylaminopyridine (2.4 mmol) at reflux temperature. The aromatic amine or heteroaromatic amine (1.2 mmol) was injected to the reaction mixture 2 h later. The mixture was stirred for another 2 h. After removing solvent in vacuo, the residue was quenched with EtOAc and water, neutralized with sat. NaHCO3 solvent, the EtOAc layer was dried over anhydrous Na2SO4 and concentrated. The residue was chromatographed on silica gel (EtOAc-petroleum ether) to give target compounds. The structures of compounds 1a-9s were showed in the Supporting information.

According to the analysis of related databases, 69695-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Ye; Lei, Chao; Xu, Xiao-Yong; Shao, Xu-Sheng; Li, Zhong; Chinese Chemical Letters; vol. 27; 3; (2016); p. 321 – 324;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 261762-56-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 261762-56-5 as follows.

Example 12 5-{[1-(4-Chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-(methoxymethyl)propyl]amino}-7-fluoro-1H-quinolin-2-one; (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 10 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After 1.5 hours at -70 1 g (6.9 mmol) N,N’-dimethoxy-N,N’-dimethyl urea in 6 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 7.5 ml of a 2 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel (ethyl acetate in hexane 0 to 30%) to yield 0.59 g 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid. 1H-NMR (CDCl3); delta=3.35 (br, 3H), 3.49 (br, 3H), 3.98 (s, 3H), 6.99 (dd, 1H), 7.13 (dd, 1H).0.44 ml (5.1 mmol) 1,1,1-trifluoro-2,3-epoxypropane in 7.5 ml THF and 2.2 ml hexane are cooled to -100 C. and 2.03 ml of a 2.5 M n-butyl lithium solution (5.1 mmol) in hexane are added over 15 minutes while the temperature does not exceed -95 C. 10 minutes after complete addition 0.57 g (2.3 mmol) 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid in 10 ml THF are added over 15 minutes while the temperature does not exceed -95 C. After 3 hours at -100 C. 2.3 ml diethyl ether is added and the reaction mixture is warmed to room temperature over 14 hours. The reaction is quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer is extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated to yield 570 mg of (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone. 1H-NMR (CDCl3); delta=2.99 (dq, 1H), 3.37 (d, 1H), 4.14 (d, 3H), 7.18 (m, 1H), 7.19 (m, 1H). 285 mg (0.95 mmol) (4-Chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone are stirred with 622 mg (1.9 mmol) caesium carbonate in 6.7 ml methanol. The reaction is quenched by addition of water after one day. The aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine, dried over sodium sulphate and then evaporated to yield 262 mg 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one. To 27 mg (0.15 mmol) 5-Amino-7-fluoro-1H-quinolin-2-one and 50 mg (0.15 mmol) 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one in 0.45 ml toluene and 0.13 ml 1,4-dioxane are added 33 mul acetic acid and 0.12 ml tetra butyl orthotitanate. The mixture is heated over 20 hours to 110 C., cooled to room temperature and poured into aqueous ammonium fluoride solution. Ethyl acetate is added and the mixture is stirred vigorously for 30 minutes. Phases are separated and two times extracted with ethyl acetate. The combined organic phases are concentrated to yield quantitatively 5-{[1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethylpropylidene]amino}-7-fluoro-1H-quinolin-2-one. The raw imine in 4.2 ml methanol is cooled to 5 C. and 120 mg sodium boron hydride are added in multiple portions over the period of 72 hours. The reaction is quenched by addition of saturated ammonium chloride solution and diluted with water and ethyl acetate. The phases are separated, the aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine and dried over sodium sulphate. After removal of the solvent preparative thin layer chromatography on silica gel (acetone in methylene chloride, 30%) yields 9.5 mg of the title compound.1H-NMR (CD3OD); delta=3.44 (s, 3H), 3.65 (m, 1H), 3.69 (d, 1H), 4.05 (d, 3H), 5.44 (s, 1H), 6.03 (dd, 1H), 6.30 (dd, 1H), 6.45 (d, 1H), 7.12 (dd, 1H), 7.35 (dd, 1H), 7.94 (d, 1H).

According to the analysis of related databases, 261762-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 39226-96-5, These common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, 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 49 N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-2-oxo-4- imidazolidinecarboxamide (E49) (in a form obtainable or prepared from (4S)-2-oxo- S-^phenylmethy^oxyJcarbonylJ^-imidazolidinecarboxylic acid); A mixture of 1-methyl-2-oxo-4-imidazolidinecarboxylic acid (144 mg, 1 mmol), N- ethyl morpholine (0.767 ml, 6.00 mmol), 1-hydroxybenzotriazole hydrate (184 mg, 1.200 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (230 mg, 1.200 mmol) in dichloromethane (18 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (210 mg, 1.000 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temperature for hours. The mixture was diluted with dichloromethane and the mixture was washed with 3N citric acid solution. The organic phase was separated, washed with brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give the N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl- 2-oxo-4-imidazolidinecarboxamide (150 mg, 55%). LC/MS [M+H]+ = 336, retention time = 2.22 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 210532-25-5, 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. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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.

General procedure: A mixture of (4-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d] pyrimidin-7-yl) methyl pivalate 6 (1.00 g, 0.0037 mol) andtriethylaminein (1.12 g, 0.011 mol) were dissolved in N,N-dimethylacetamide(10 ml), followed by addition of various sulfonyl chloride(0.0044 mol) and was stirred at 60 C for 4 h. The reaction mixture waspoured into ice water (50 ml). The residue was filtered and washed withwater, and dried to give compounds 7a-7p.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Feng; Zang, Linghe; Miao, Xiuqi; Jia, Fang; Wang, Jie; Zhu, Minglin; Gong, Ping; Jiang, Nan; Zhai, Xin; Bioorganic and Medicinal Chemistry; vol. 27; 18; (2019); p. 4089 – 4100;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, 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 139512-70-2, Quality Control of 4-Chloro-5-fluorobenzene-1,2-diamine

Intermediate compound 5 (0.2 g, 1.24 mmol) and oxamide 6c (0.11 g, 1.24 mmol) were weighed and dissolved in 15 mL glacial acetic acid: methanol (3:2). This mixture was refluxed for 4hr. After completion of reaction (monitored by TLC), the organic solvent was evaporated. The obtained residue were dissolved in dichloromethane and washed with water. The organic solvent was dried and evaporated to obtain solids which were recrystallized from ethanol. (yield 84%, m.p. 210-212 C). 1H NMR (400 MHz, CDCl3), delta ppm, 4.0 (s, 4H, -NH2 at C-2 and C-3), 7.7384 (d, J = 9.3 Hz, -H at C-5), 8.0932 (d, J = 7.6 Hz, -H at C-8). 13C NMR (400 MHz, CDCl3), delta ppm, 109.2, 119.7, 125.0, 132.8, 135.1, 153.1, 153.8, 159.4. Mass (ESI), C8H6ClFN4, M+ and [M+2]+ peaks were found at 212 and 214, respectively.

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, 4-Chloro-5-fluorobenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Patel, Saloni B.; Patel, Bhumika D.; Pannecouque, Christophe; Bhatt, Hardik G.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 230 – 240;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, 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. name: 3,5-Dibromochlorobenzene

Compound 1 (30 g, 100 mmol) was dissolved in anhydrous i-Pr2O (300.0 mL) in a dried flask under nitrogen. The reaction mixture was cooled to -78 C and stirred under nitrogen atmosphere. A 2.5 M solution of n-BuLi in hexanes (40 mL, 100 mmol) was added dropwise to the above solution and the reaction mixture was stirred at -78 C for 30 min after complete addition of n-BuLi. N-methoxy-N-methylacetamide (12 g, 120.0 mmol) was added to the above reaction mixture, while keeping the reaction mixture below -78 C. After addition of N-methoxy-N-methylacetamide was completed, the reaction mixture was warmed slowly to room temperature for 30 min. The reaction mixture was poured into 40 mL of aqueous NH4Cl and the reaction mixture was stirred for 15 min. The organic phase was separated, dried over anhydrous MgSO4, filtered and evaporated in vacuo to give the compound 2 (25 g, crude) as a pale yellow viscous liquid.

The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAINT LOUIS UNIVERSITY; RUMINSKI, Peter; GRIGGS, David; WO2014/15054; (2014); 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. 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3BrClF3O

General procedure: To a solution of Compound 6A (138 mg, 0.32 mmol) in tolunen (4 mL) was added N-methylpiperazine (160 mg, 1.6 mmol), t-BuONa (61 mg, 0.64 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), and Xantphos (37 mg, 0.064 mmol) and heated in a microwave oven at 120 C for 2 hours. The mixture was concentrated and purified by reverse phase column chromatography to afford Compound 6B. LC-MS (ESI) m/z: 440 [M+H]+.

According to the analysis of related databases, 468075-00-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 7051-16-3, 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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 26A 5-chlorobenzene-1,3-diol A solution of 5-chloro-1,3-dimethoxybenzene (5.41 g, 31.3 mM) in methylene chloride (75 mL) at -78 C. was stirred with a 1M solution of BBr3 in methylene chloride (63 mL) for 45 minutes. The reaction was allowed to warm to room temperature overnight and diluted with water (75 mL). The layers were separated and the aqueous layer washed two times with methylene chloride. The aqueous layer was acidified with 1N HCl and extracted 3 times with ethyl acetate. The combined organic layers were washed with 1N sodium thiosulfate (1*35 mL) and water (1*25 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure and purified by chromatography (methylene chloride/acetone) to provide the titled compound. MS ESI(-)) m/e 143 (M-H)+; 1H NMR (300 MHz, CDCl3) delta 6.45 (d, 2H), 6.25 (t, 1H), 5.41 (bs, 2H).

The synthetic route of 1-Chloro-3,5-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US6972340; (2005); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

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, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); 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. 102-49-8, name is 3,4-Dichlorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

Example 1: N-(3,4-dichlorobenzvl)-4-methvlpiperazine-l-carboxamideTo a solution of 3,4-dichlorobenzylamine (0.195 g, 1.11 mmol) and diisopropylethylamine(0.193 mL, 1.11 mmol) in 4 mL of THF was added a preformed solution of 4-nitrophenylchloroformate (0.223 g, 1.11 mmol) in 4 mL of THF. The reaction mixture was stirred at RTfor 3.5 h. To this solution was added N-methyl piperazine (0.442 g, 4.42 mmol) and theresulting solution was stirred at RT for 16h. The reaction mixture was concentrated underreduced pressure, diluted with EtOAc (50 mL) and the solution was washed with saturatedaqueous sodium bicarbonate (2 x 50 mL) and brine (50 mL). The solvent was removed underreduced pressure and the residue was subjected to supercritical fluid chromatography (21 mmx 150 mm diol-bonded SiC>2 (6|J,m particle size), isocratic method, 25percent MeOH (containing0.5percent isopropyl amine) in CO2) to afford the title compound as a pale yellow solid (0.245 g,73percent). MS m/z 302.2 (M+H)+; .H NMR (300.1 MHz, DMSO-d6) 52.17 (s, 3H), 2.22-2.26(m, 4H), 3.25-3.31 (m, 4H), 4.20 (d, J=5.8Hz, 2H), 7.12 (t, J=5.8Hz, 1H), 7.23 (dd, .7=8.2,2.0Hz, 1H), 7.47 (d, J=1.8Hz, 1H), 7.56 (d, /=8.2Hz, 1H).

According to the analysis of related databases, 102-49-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2006/14135; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics