Tag: M.W=100-200

Application of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

General procedure: To a stirred solution of 5-chloro-2-ethylpyrazolo[1,5-a]pyridine-3-carboxylic acid or 2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (1.34mmol) in DMF (20mL) was added EDCI (0.39g, 2.01mmol), HOBt (91mg, 0.67mmol) and Et3N (0.68g, 6.7mmol) at room temperature. After 1h of stirring, 1a-8a (1.34mmol) was added and the reaction was heated to 80C for overnight. The mixture was cooled, and diluted with EA (50mL), washed with water and brine, dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography to afford the title compounds1-8.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Xiaoyun; Tang, Jian; Cui, Shengyang; Wan, Baojie; Franzblauc, Scott G.; Zhang, Tianyu; Zhang, Xiantao; Ding, Ke; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 41 – 48;,
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Related Products of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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.

0.500 g of cinnamic acid, 0.295 g of 1,11-diamino-3,6,9-trioxadecane, 0.647 g of EDCI, 0.037 g of DMAP, 10 mL of anhydrous dichloromethane were sequentially added to the round bottom flask, and stirred at room temperature. After 12 h, 20 mL of dichloromethane was added, and the mixture was washed successively with brine (1×30 mL) and water (2×30 mL), dried over anhydrous sodium sulfate, filtered, evaporated to dryness Chloroform/methanol = 35:1; 50:4) gave 0.178 g of a pale yellow oily substance, yield 28% (see Figure 49 for the synthetic route and Figure 50 for the characterization)

Statistics shows that 1,11-Diamino-3,6,9-trioxaundecane is playing an increasingly important role. we look forward to future research findings about 929-75-9.

Reference:
Patent; Chinese Academy Of Medical Sciences Biomedical Engineering Institute; Liu Tianjun; Wang Jiawen; Li Guoliang; Hong Ge; Wang Wenzhi; (37 pag.)CN110229110; (2019); A;,
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Reference of 2734-70-5, 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 2734-70-5 as follows.

To a mixture of Compound 4b (0.37 g, 3.9 mmol) and 2,6-dimethoxyaniline (0.5 g, 3 mmol) in toluene (5 mL), at 0° C., was added a 2M solution of trimethylaluminum in hexane (2 ml, 4 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and heated at 110° C. overnight. The reaction mixture was allowed to cool to RT and quenched with saturated aqueous Rochelle’s salt and EtOAc. The phases were separated, the aqueous phase was extracted with EtOAc. The organic phases were combined and washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0 to 30percent MeOH/0.5percent TEA in DCM to give Compound 4c (0.35 g, 44percent yield) as an orange oil. MS m/z=249.4 (M+H). 1H NMR (methanol-d4) delta 7.01 (t, J=8.3 Hz, 1H), 6.64 (d, J=8.3 Hz, 2H), 2.29-2.48 (m, 2H), 1.50-1.67 (m, 2H), 0.78-0.93 (m, 1H), 0.44 (s, 2H), 0.02-0.16 (m, 2H).

According to the analysis of related databases, 2734-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Pi, Zulan; Bilder, Donna M.; Brigance, Robert Paul; Finlay, Heather; Jiang, Wen; Johnson, James A.; Lawrence, R. Michael; Meng, Wei; Myers, Michael C.; Phillips, Monique; Tora, George O.; Zhang, Xiaojun; (59 pag.)US2017/275272; (2017); A1;,
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Synthetic Route of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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 42.3: N*6*-tert-butyl-2-chloro-N*8*-(2,4-dimethoxy-benzyl)-9-(tetrahydro-pyran-2-yl)- 9H-purine-6,8-diamine (Buchwald type amination, Method E) A solution of [8-Bromo-2-chloro-9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]-tert-butyl-amine (compound of Step 41.2, 77 mg, 0.2 mmol), 2,4-dimethoxybenzylamine (40 mg, 0.24 mmol), potassium phosphate tribasic (60 mg, 0.28 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (8 mg, 0.02 mmol), and Pd2(dba)3 (9 mg, 0.02 mmol) are stirred in dimethoxyethane (0.5 mL) under argon for 20 h at 100C. The reaction mixture is cooled to RT, diluted with ethyl acetate, washed with 10% sodium bicarbonate, and brine. The combined organic phases are dried over sodium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (CombiFlashNo. Companion RediSep column hexane/ethyl acetate gradient 20: 1 to 4: 1) to afford N*6*-tert-butyl-2-chloro-N*8*-(2,4- dimethoxy-benzyl)-9- (tetrahydro-pyran-2-yl)-9H-purine-6,8-diamine (55 mg, 58%), HPLC tR : 6.03, (M+H)+ = 475.1.

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
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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. 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H13NO

A mixture of phenyl 5-({trans-4-[(2-chloro-4,5-difluorophenyl)carbamoyl]cyclohexyl}carbamoyl)-1 H-im idazole-4-carboxylate (100 mg, 0.199 mmol,) and 2-methoxy-2-methylpropan-1 -amine (103 mg, 0.994 mmol, GAS No 89282-70-2) in tetrahydrofuran (5.0 ml) was stirred at 600 ove r night. For work-up, the reaction mixture was concentrated and the residue was first purified by flash chromatography (10 g Snap Gartridge, ethyl acetate/ethanol gradient, 0% -> 5% ethanol) followd by purification withpreparative HPLG (Method 9) to yield the title compound (46.0 mg, 45% yield).LG-MS (Method 3): R = 1.15 mm; MS (ESIpos) m/z = 512.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 13.38-13.09 (m, 1H), 11.25-1 0.90 (m, 1H), 9.67-9.53 (m, 1H), 8.52-8.25 (m, 0.5H), 8.21-7.95 (m, 0.5H), 7.87-7.75 (m, 3H), 3.92-3.59 (m, 1H),3.37 (d, 2H), 3.15 (5, 3H), 2.15-1.77 (m, 4H), 1.65-1.20 (m, 4H), 1.14 (5, 6H).

According to the analysis of related databases, 89282-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2688-84-8, name is 2-Phenoxyaniline, 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 2688-84-8, category: ethers-buliding-blocks

According to Scheme 34, intermediate 5-a was synthesized:2-Penoxyaniline (25.0, 0.135 mol), 30 ml of hydrochloric acid and 150 ml of water were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 C and stirred for 1 hour.At the same temperature, 75 ml of an aqueous solution of sodium nitride (11.2 g, 0.162 mol) was added dropwise, followed by stirring for 1 hour.75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise noting the temperature of the reaction solution not to exceed 5 degrees. After stirring for 5 hours at room temperature, the reaction was completed, washed with sodium thiosulfate aqueous solution and extracted with ethyl acetate and water.The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain Patent; SFC Ltd.; Cha Sun-uk; Jeong Gyeong-seok; Song Ju-man; Lee Yu-rim; Park Sang-u; Kim Hui-dae; Park Seok-bae; (65 pag.)KR2019/111856; (2019); A;,
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Application of 24332-20-5,Some common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, molecular formula is C5H12O3, 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 3: (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione A round bottom flask was charged with 2-methoxyacetaldehyde dimethyl acetal (2076 mul, 2076 mumol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (299 mg, 2076 mumol). The flask was fitted with a reflux condenser and the mixture was heated at 100 C. for 2 h under nitrogen. 5,6-Dimethoxypyridin-3-amine (320 mg, 2076 mumol) was added, and within a minute a solid had precipitated out of solution. The heterogeneous mixture was heated at 100 C. for 10 min. The mixture was cooled to RT and the solids were filtered and washed with hexanes. (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was isolated as a yellow/orange solid. MS [M+H]=309.

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

Reference:
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
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Related Products of 36865-41-5, 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. 36865-41-5 name is 1-Bromo-3-methoxypropane, 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.

A mixture of l-bromo-3-methoxypropane (2.5 g, 16.34 mmol) and sodium sulfite (2.06 g, 16.34 mmol) in water (25 mL) was heated at reflux for 24 h. The solvent was evaporated and the formed solid was washed with a mixture of diethyl ether/toluene (8:2) and dried in vacuo. The solid was added in portions to phosphorus oxychloride (25 mL) and heated at 80 0C for 5 h and then at 100 0C for 2 h. The mixture was cooled to room temperature, diluted with dichloromethane and filtrated. The filtrate was concentrated, ethyl acetate was added followed by ice. The ice was allowed to melt and the organic phase was collected, washed with water and brine, dried over sodium sulfate and concentrated to give 2.8 g (100% yield) of the title compound: 3.35 (t, J= 6.53 Hz, 2 H), 3.20 (s, 3 H), 2.44 – 2.49 (m, 2 H), 1.74 – 1.81 (m, 2 H).

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

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/58602; (2007); A2;,
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Electric Literature of 22236-10-8,Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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 31; 2-ButyI-5-(3-chlorophenyl)-4-{[4-(difluoromethoxy)phenyl]amino}isothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-(3-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide (0.25Og, 0.75mmol) and 4-(difluoromethoxy)aniline (0.238g, 1.50mmol) were mixed in MeCN (2mL) and heated in a microwave reactor at 160C for 60 mins. The reaction mixture was evaporated and the residue was purified on a Horizon TM flash system using Heptane and EetOAc as eluant giving the title compound (0.25g, 72.9%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Difluoromethoxy)aniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
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Electric Literature of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of (+/-)-8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl) methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.; Example 2 Preparation of (+/-)-6-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl)methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMR Technology, Inc.; US2007/21408; (2007); A1;,
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