Month: May 2021

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. 622-86-6, name is (2-Chloroethoxy)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H9ClO

Example 1233-{[(frans-4-Methylcyclohexyl)carbonyl][2-(phenyloxy)ethyl]amino}-1-(4-pyrazolo[1,5- a]pyrimidin-2-ylphenyl)-1H-pyrazole-4-carboxylic acidTo Intermediate 119 (200 mg) was added anhydrous DMF (8 mL), and the resulting suspension was stirred at room temperature, under nitrogen for 5 minutes. Sodium hydride (60% dispersion in mineral oil) (34 mg) was then added, and the reaction mixture stirred at room temperature, under nitrogen for 25 minutes. Beta-chlorophenetole (331 mg) was added, and the reaction was stirred at 5O0C, under nitrogen for 20 h. Water (2 mL) was added to quench the reaction, and the mixture was stirred for 15 minutes before the solvent was removed by evaporation. The residue was then suspended in THF (2 mL) and ethanol (2 mL), and 2M lithium hydroxide solution (2 mL) was then added. The reaction mixture was stirred at room temperature for 24 h, and then neutralised using 2M HCI, and partitioned between water and DCM. The layers were stirred for 30 minutes, and then separated using a hydrophobic frit. The organic phase was then concentrated by evaporation, and purified using ISCO Companion C18 chromatography eluting with a gradient of acetonitrile (containing 0.05% formic acid) in water ( containing 0.1% formic acid) to give the title compound. MS calcd for (C32H32N6O4+H)+: 565 MS found (electrospray): (M+H)+= 565

The synthetic route of 622-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/39146; (2007); 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. 29671-92-9, name is Carbamimidic chloride hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: CH4Cl2N2

The mixture of compound 1 (50 g, 0.318 mol), compound 2 (54.86 g, 0.477 mol) and methylsulfonylmethane (150.6 g, 1.59 mol) was refluxed overnight, cooled and evaporated. The resulting residue was washed mixture EtOAc-iPrOH (1 : 2). The yield was 41.65 g (0.249 mol, 78%).

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; SHY THERAPEUTICS LLC; HADARI, Yaron R.; CARTA, Luca; SCHMERTZLER, Michael; WILLIAMS, Theresa M.; REYNOLDS, Charles H.; HUTCHESON, Rebecca; (1452 pag.)WO2018/237084; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 75717-77-0, name is 2,4-Dichlorophenylacetylene, 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. COA of Formula: C8H4Cl2

Was added quinoline (65 ~ 84.5mg, 0.5 ~ 0.65mmol) in a round bottom flask, 2,3-dichlorobenzene acetylene (85mg, 0.5mmol), trifluoromethyl propiolate (114mg, 0.75mmol), cuprous iodide (9.5mg, 10% mol), dichloromethane(5mL) as a solvent, at room temperature for 24 to 30 hours; then spin dry instead of dimethyl sulfoxide as solvent, was added copper bromide (11.2mg, 10% mol), 4- dimethylaminopyridine (12.2mg, 20% mol) 100 ~ 120 after heating the reaction to 18 to 24 hours,After cooling to room temperature with saturated brine and extracted three times with ethyl acetate, the organic layers were spin-dry column chromatography to give the pure productionThereof. As a pale yellow solid. Yield 52%.

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

Reference:
Patent; Shanghai University; Xu, Zhiliang; Chen, Jie; Han, Jing; Zhang, Hui; Cao, Weiguo; (19 pag.)CN105669667; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-48-9, A common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, 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.

To a solution of 2,4-Dichloro-1-fluorobenzene (8.0 g, 48.5 mmol) in THF (63 mL) n-BuLi (23.27 mL, 2.5 M, 43.6 mmol) was added dropwise at -78 C and stirred for 1.5 h. To the mixture Sulfur (3.1 g, 72.7 mmol) was added at -78 C and stirring for 2 h. To the resulting mixture 10% Hydrochloric acid (HCl) was added to adjust pH to 5-6. The resulting mixture was extracted with EtOAc (200 mL * 3), the combined organic phase was washed with brine (100 mL * 2), dried over Na2SO4. After filtered, the organic phase was concentrated to dry to give compound 31 as yellow oil (11.4 g, 99.0% yield). 1H NMR (400 MHz, CDCl3) delta 7.31-7.19 (m, 1H, Ar-H), 6.95-6.89 (t, 1H, Ar-H), 4.69 (s, 1H, SH).

The synthetic route of 1435-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Na; Wang, Yanfen; Huang, Gongchao; Ji, Conghui; Fan, Wei; Li, Haitao; Cheng, Ying; Tian, Hongqi; Bioorganic Chemistry; vol. 65; (2016); p. 146 – 158;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13918-92-8, The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

General procedure: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

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-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 41965-95-1, 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. 41965-95-1 name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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 N: Amide coupling (10):In a glass vial, under inert atmosphere (N2), to a solution of the carboxylic acid (1.0 eq.) in CH2CI2 (0.25 M) were added HOBt (1.20 eq.), DMAP (0.25 eq.), EDC HCI (2.5 eq.) and DIPEA (4.0 eq.). The reaction mixture was stirred at rt for 30 min. An amine (2.0 eq.) was then added and the reaction mixture stirred at rt until completion of the reaction. DMF (0.3 vol. CH2CI2) and PL-SO2CI2 (1.0 eq.) were added and after stirring at rt for 1 h the mixture was filtered (CH2CI2) and concentrated under reduced pressure. Purification of the residue by FC or HPLC gave the desired compound.; Example 374:(Sf^-Lambda/^S-Chloro^-methoxyphenyl-methyO-tef^-Lambda^^-pyrrolidino-butyO^S*^/?*)- [4,7-ethenylene-spiro[2.4]heptane]-5,6-dicarboxamide, formate salt:Following general procedure N, starting from (5R*)-5-hydroxycarbonyl-(6R*)-Lambda/6-(4- pyrrolidin-1-yl-butyl)-(4S*,7/?*)-[4,7-ethenylene-spiro[2.4]heptane]-6-carboxamide and 3- chloro-4-methoxybenzylamine hydrochloride.LC-MS-conditions FA: tR = 0.75 min; [M+H]+ = 486.24.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-methoxybenzylamine Hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; CORMINBOEUF, Olivier; CREN, Sylvaine; GRISOSTOMI, Corinna; LEROY, Xavier; RICHARD-BILDSTEIN, Sylvia; WO2010/134014; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Formula: C7H7ClFN

To a solution of (4-chloro-3-fluorophenyl)methanamine (266 mg, 1.67 mmol, Alfa) in a methanol buffer (3.6 weight % sodium acetate trihydrate and 2.4 weight % acetic acid in methanol, l5mL) was added 1,4-dioxane-2,5-diol (100 mg, 0.833 mmol, Aldrich) in one portion followed by sodium cyanoborohydride (105 mg, 1.67 mmol) and trifluoroacetic acid (0.1 mL). After stirring at ambient temperature for 10 minutes, the reaction mixture was concentratedunder reduced pressure to less than 5 mL and was filtered through a glass microfiber frit, and then purified by preparative HPLC [YMC TriArtTM Cl 8 Hybrid 5 jim column, 50 x 100 mm, flow rate 140 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (0.18 g, 0.88 mmol, 53.0 % yield). MS (ESf?) nilz 204 (M+H).

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; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen Ann; SIDRAUSKI, Carmela; FROST, Jennifer M.; SHI, Lei; TONG, Yunsong; DART, Michael J.; MURAUSKI, Kathleen; (213 pag.)WO2019/90088; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29027-20-1, name is 3-Chloro-5-methylaniline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 29027-20-1

to the mixture of solid (400 mg, 1.66 mmol) from Step 2-1 and MeOH (15 mL) was added 3-chloro-5-methylaniline (0.21 mL, 1.66 mmol), formic acid (0.064 mL, 1.66 mmol) and l-(2,2-dimethoxy-ethyl)-2- isocyano-benzene ( 0.32 mL, 2.5 mmol). The resulting mixture was heated at 50 C overnight. The reaction solution was concentrated and dried under high vacuum to give brown solid as the desired product (60% pure). The crude material was used for next step without further purification.

The synthetic route of 29027-20-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRINETICS PHARMACEUTICALS, INC.; ZHAO, Jian; ZHU, Yunfei; WANG, Shimiao; HAN, Sangdon; KIM, Sun Hee; (109 pag.)WO2017/3724; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39226-96-5, 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. 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3) N-(2-chloro-3-(trifluoromethyl)benzyl)-3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxamide To a solution of amine (500 mg, 2.39 mmol, 1.0 eq) and acid (397 mg, 2.39 mmol, 1.0 eq) in DMF (15 mL) were added DIEA (1.54 g, 11.9 mmol, 5 eq) and HBTU (1.09 mg, 12.87 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aqHCl (1*20 mL), sat NaHCO3 (1*20 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C16H16ClF3N3O: 358.0 (M+H), Found 358.0.

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-Chloro-3-(trifluoromethyl)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 63624-28-2,Some common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, molecular formula is C8H9ClO4S, 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.

301 mg of the compound obtained in step 16-2 (diastereoisomer mixture) was added under ice cooling and a nitrogen atmosphere to a 3 mL tetrahydrofuran solution of 26 mg of sodium hydride, and the reaction mixture was stirred for 20 minutes. After this, a 2 mL tetrahydrofuran solution of 170 mg of 2,4-dimethoxybenzenesulfonyl chloride was added dropwise, and the reaction mixture was stirred for 2 hours at room temperature. Then 5mL of ethylacetate and 10mL of a 5% potassium carbonate aqueous solution were added and the reaction mixture was stirred for 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (10 mL × 3), and the combined organic layer was dried with sodium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone = 99/1; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 115 mg (isomer A: colorless, amorphous) and 127 mg (isomer B: colorless, amorphous). Isomer A: [alpha]D25 = -248 (c = 0.183, chloroform) MS (ESI pos.) m/z : 680([M+H]+), (ESI pos.) m/z : 702([M+Na]+ 1H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.89 (s, 1 H), 2.19 – 3.94 (m, 21 H), 4.65 – 5.06 (m, 1 H), 5.23 – 5.44 (m, 1 H), 6.43 (s, 1 H), 6.57 (dd, J =9.0, 2.3 Hz, 2 H), 6.97 – 7.05 (m, 1 H), 7.42 (d, J=8.8 Hz, 1 H), 7.75 (s, 1 H), 7.93 (d, J=8.5 Hz, 1 H), 8.09 – 8.20 (m, 1 H) Isomer B: [alpha]D25 = +211 (c = 0.200, chloroform) MS (ESI pos.) m/z : 680([M+H]+), (ESI pos.) m/z : 702([M+Na]+) 1 H-NMR (499 MHz, CDCl3) delta (ppm) ; 1.88 – 2.23 (m, 2 H), 2.33 (s, 3 H), 2.55 – 2.81 (m, 6 H), 3.36 (s, 3 H), 3.47 – 3.63 (m, 1 H), 3.79 – 3.88 (m, 7 H), 4.07 – 4.19 (m, 1 H), 4.95 – 5.19 (m, 1 H), 6.48 (d, J=2.1 Hz, 1 H), 6.57 (dd, J=8.8, 2.1 Hz, 1 H), 6.63 (d, J=8.2 Hz, 1 H), 6.99 – 7.07 (m, 1 H), 7.41 – 7.48 (m, 1 H), 7.67 (s, 1 H), 7.92 – 8.01 (m, 1 H), 8.13 (d, J=8.8 Hz, 1 H)

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1659121; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics