Category: ethers-buliding-blocks

Application of 10578-75-3,Some common heterocyclic compound, 10578-75-3, name is 2-(Benzyloxy)ethanamine hydrochloride, molecular formula is C9H14ClNO, 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.

2,4-Dichloro-6,7-dimethyl-3-nitropyridine (26.89 g, 121.7 mmol), anhydrous N,N-dimethylformamide (400 mL), anhydrous triethylamine (48.84 mL), and the benzyloxyethylamine hydrochloride salt (27.4 g, 146.0 mmol) from Part B were combined under nitrogen and heated to 90 C. for 20 minutes, 60 C for 1 hour, and then 90 C. for 1 hour. The reaction was complete as determined by TLC analysis using 8/2 hexane/ethyl acetate. The reaction mixture was concentrated under reduced pressure, and the resulting orange solids were triturated with water. The resulting solids were filtered off and recrystallized from ethyl acetate. Recrystallized solids were rinsed with hexane and dried under vacuum at 50 C. for 30 minutes to provide 21.8 g of yellow fluffy solid for use in the next step. NMR analysis confirmed the N-[2-(benzyloxy)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine and a minor amount of residual salts.; Under a nitrogen atmosphere, triethylamine (40.4 mL, 290 mmol) was added to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (12.0 g, 58.0 mmol), prepared according to the general method of Part A of Example 1 using 2,4-dihydroxy-6-methyl-3-nitropyridine in lieu of 2,4-dihydroxy-5,6-dimethyl-3-nitropyridine, in anhydrous N,N-dimethylformamide (DMF) (200 mL). To the resulting dark brown solution was added 2-(benzyloxy)ethylamine hydrochloride (11.97 g, 63.76 mmol), and the mixture was stirred at room temperature for 23 hours. The volatiles were then removed under reduced pressure, and the residue was mixed with water and ethyl acetate. The organic layer was washed with water (3×200 mL), aqueous sodium bicarbonate (2×200 mL), and brine (3×250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil. The crude product (18.1 g) was purified by column chromatography on silica gel (700 g, eluting with 80:20 hexane:ethyl acetate) to provide an oil which was triturated with 80:20 hexane:ethyl acetate. The resulting crystals were isolated by filtration and dried to provide 4.7 g of [2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine as a yellow solid.

The synthetic route of 10578-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 57602-02-5, name is 1,14-Dibromo-3,6,9,12-tetraoxatetradecane, 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 57602-02-5, category: ethers-buliding-blocks

1,14-dibramo-3,6,9,12-tetraoxatetradecane (3.35 g, 9.2 mmol) and sodium methanethiosulfonate (2.48 g, 18.5 mmol) were dissolved in dry DMF (40 mL) and stirred at room temperature for 3 days. The solvent was evaporated. The residue was purified by column chromatography on SiO2. Elution with ethyl acetate/hexane (9:1) afforded, after evaporation, 1-(14-bromo-3,6,9,12-tetraoxatetradecyl) methanethiosulfonate (0.85 g) as a pale yellow oil and tetraoxatetradecane-1,14-diyl-bis-methanethiosulfonate (useful as a cross linker) as a slightly yellow colored oil (1.64 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,14-Dibromo-3,6,9,12-tetraoxatetradecane, and friends who are interested can also refer to it.

Reference:
Patent; Dime, David S.; Backx, Peter; Kimmeldirk, Klaus; EP966304; (2005); B1;,
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Electric Literature of 121588-79-2, A common heterocyclic compound, 121588-79-2, name is trans-4-Methoxycyclohexanamine, molecular formula is C7H15NO, 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 mixture of 5-chloro-6-ethyl-3-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino}pyrazine-2-carboxamide (11,100 mg, 0.205 mmol) and NMP (1.5 mL) was added (1r,4r)-4-methoxycyclohexan-1-amine (106 mg, 0.820 mmol), and the mixture was irradiated with microwaves at 200 C for 30 min. After the mixture was cooled, saturated aqueous NaHCO3 solution was added, and the resulting slurry was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo.The residue was purified by silica gel column chromatography (CHCl3/MeOH/28% aqueous NH3=100:0:0 to 200:10:1). The resulting product was solidified from EtOAc, filtered and dried to give 12c (62 mg,52%) as a yellow solid. 1H NMR (DMSO-d6): delta 1.10-1.28 (2H, m), 1.18(3H, t, J=7.4 Hz), 1.33-1.63 (4H, m), 1.73-1.86 (2H, m), 1.89-2.00(2H, m), 2.00-2.11 (2H, m), 2.14 (3H, s), 2.18-2.64 (11H, m), 2.56(2H, q, J=7.3 Hz), 3.05-3.19 (1H, m), 3.22-3.39 (2H, m), 3.26 (3H, s),3.75-3.95 (1H, m), 3.80 (3H, s), 6.66 (1H, d, J=7.6 Hz), 6.78 (1H, d,J=8.4 Hz), 7.05 (1H, d, J=2.4 Hz), 7.18 (1H, d, J=2.8 Hz), 7.24(1H, dd, J=2.4, 8.8 Hz), 7.50 (1H, d, J=2.8 Hz), 11.01 (1H, s); MS(ESI) m/z [M+H]+ 581; HRMS (ESI) m/z Calcd for C31H49N8O3[M+H]+: 581.3922, Found: 581.3924.

The synthetic route of 121588-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
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Adding a certain compound to certain chemical reactions, such as: 172282-50-7, name is 4-(Difluoromethoxy)benzene-1,2-diamine, 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 172282-50-7, Safety of 4-(Difluoromethoxy)benzene-1,2-diamine

Dissolve 8.1 g of 4-difluoromethoxy-o-phenylenediamine in 30 mL of methanol, directly add 35 mL of carbon disulfide and 3.0 g of sodium hydroxide, stir, heat to reflux, and hold for 4 h.Reduce the temperature to room temperature, add 30ml of water, then adjust the pH value to 4 with 10% hydrochloric acid, flocculent precipitates appear, and filter to obtain the crude 2-mercapto-5-difluoromethoxybenzimidazole.Add the obtained crude 2-mercapto-5-difluoromethoxybenzimidazole to a 100 mL flask, and then add 3.0 g of sodium hydroxide, 30 mL of water and 1 g of activated carbon, heat to 80 C, and hold for 1 h.Hot filtration. When the temperature of the filtrate drops to room temperature, adjust the pH value to 4 with a concentration of 10% hydrochloric acid, flocculent precipitates appear, filter,The obtained solid (precipitation) was washed with water to neutrality and dried to obtain a white solid product, 2-mercapto-5-difluoromethoxybenzimidazole, with a yield of 94.5%, a melting point of 260.1-261.5 C, and a purity of more than 99%.

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-(Difluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui Jin He Industrial Co., Ltd.; Jiang Weiqiang; Chen Chaohui; Sha Lifeng; (6 pag.)CN110590576; (2019); A;,
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13353-03-2, name is 2,4,6,8-Tetraoxanonane, belongs to ethers-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. Application In Synthesis of 2,4,6,8-Tetraoxanonane

2.7 mol of dimethoxymethoxymethane, 0.5 mol of 2,6-methylethylaniline and 100 mLBenzene was added to the reaction flask and incubated at 75-80 C for 18 h.After the completion of the reaction, the methoxymethanol and benzene recovered were separated and separated.Distillation gives 2,6-methyl-N-(methoxymethoxymethyl)aniline,The yield was 97.2% and the content was 98.9%.The total yield of the above two steps was 93.51%.

The synthetic route of 13353-03-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Binnong Technology Co., Ltd.; Xu Jiajun; Sheng Qingquan; Zhang Jun; (7 pag.)CN110183334; (2019); A;,
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Reference of 121588-79-2, These common heterocyclic compound, 121588-79-2, name is trans-4-Methoxycyclohexanamine, 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 DMF (2 mL) solution of (trans)- 3-(5-fluoro-2- methoxyphenoxy)cyclobutanecarboxylic acid (Intermediate 69) (50 mg, 0.21 mmol) was added HATU (1 19 mg, 0.312 mmol) and N,N-diisopropylethylamine (0.1 1 mL, 0.62 mmol). After 10 minutes, 4-((frans)-4-aminocyclohexyl)morpholin-3-one (Intermediate 73) (41 mg, 0.21 mmol) was added, and the mixture was stirred for 2 h, diluted with water and MeOH, and loaded onto a semi-prep HPLC (NH4OH as modifier) to afford the title compound as a light tan solid (43 mg, 49%). 1H NMR (400 MHz, CD3OD) delta 1 .26-1 .41 (m, 2 H), 1 .60-1 .70 (m, 4 H), 1 .90-1 .99 (m, 2 H), 2.29-2.41 (m, 2 H), 2.59 (ddd, J = 13, 7, 4 Hz, 2 H), 3.04 (dt, J = 10, 5 Hz, 1 H), 3.27 (dt, J = 3, 2 Hz, 2 H), 3.29-3.34 (m, 2 H), 3.56-3.62 (m, 1 H), 3.77 (s, 3 H), 3.80-3.86 (m, 2 H), 4.08 (s, 2 H), 4.25-4.34 (m, 1 H), 6.48-6.61 (m, 2 H), 6.87 (dd, J = 9, 5 Hz, 1 H); LC-MS (LC-ES) M+H = 421 .

The synthetic route of 121588-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17715-70-7, name is 2,4-Dimethoxy-1-fluorobenzene, 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 17715-70-7, HPLC of Formula: C8H9FO2

A solution of 1-fluoro-2,4-dimethoxybenzene (0.25 g, 1.60 mmol) in 5 mL of CH2Cl2 under Ar atmosphere was cooled to 0 C, then TiCl4 (neat, 0.38 mL, 3.52 mmol) was slowly added. The reaction mixture was left to react for 30 min. Dichloromethyl methyl ether (0.21 mL, 2.40 mmol) was added and the mixture left to react for a further 30 min. The reaction was quenched by the addition of saturated aq. NH4Cl (10 mL) and diluted with CH2Cl2 (10 mL). The mixture was left to stand for 30 min and the organic phase was separated and washed with 0.1 M HCl, saturated aq. NaHCO3 and brine. The organic layer was dried with Na2SO4, filtered and concentrated in vacuo to give crude product which was purified by PTLC with 30% EtOAc/hexanes as eluent to give 5-fluoro-2,4-dimethoxybenzaldehyde as a white solid (0.24 g, 1.30 mmol, 88 %).

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:
Article; Radomkit, Suttipol; Sarnpitak, Pakornwit; Tummatorn, Jumreang; Batsomboon, Paratchata; Ruchirawat, Somsak; Ploypradith, Poonsakdi; Tetrahedron; vol. 67; 21; (2011); p. 3904 – 3914;,
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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. 888318-22-7, name is 1-Bromo-3,4-difluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrF2O

To a flask containing 1-bromo-3,4-difluoro-2-methoxy-benzene (1.0 g, 4.48 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (0.71 g, 4.93 mmol) in 1,4-dioxane (10 ml) was added tBuONa (1.3 g, 13.44 mmol), Pd2(dba)3 (82 mg, 0.09 mmol) and Ru-Phos (84 mg, 0.18 mmol)under N2. After being heated with stirring at 100 C overnight, the reaction mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8- (3 ,4-difluoro-2-methoxy-phenyl)- 1 ,4-dioxa- 8-azaspiro [4.5] decane (0.74 g), which was used in the next step without further purification.

According to the analysis of related databases, 888318-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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Related Products of 456-55-3,Some common heterocyclic compound, 456-55-3, name is (Trifluoromethoxy)benzene, molecular formula is C7H5F3O, 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.

(iv) 4-Trifluoromethoxy-alpha,alpha,alpha-trifluoroacetophenone, from 4-bromotrifluoromethoxybenzene 4-Bromotrifluoromethoxybenzene may be prepared from trifluoromethoxybenzene by the process described in the Journal of Organic Chemistry, 29, 1, (1964). Boiling point: 164-166 C. (atmosphere pressure). 1 H NMR (CDCl3) (ppm): 7.35, 8.14 (4H,d) 19 F NMR (CDCl3) (ppm relative to CFCl3): -58.1 (s) CF3 O -72.1 (s) CF3

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

Reference:
Patent; Imperial Chemical Industries PLC; US5225607; (1993); A;,
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Related Products of 17600-72-5,Some common heterocyclic compound, 17600-72-5, name is 1-Ethoxy-2-methoxybenzene, molecular formula is C9H12O2, 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 aryl methyl ether (20 mmol) and 47% aqueous HBr (4.5 mmol equiv. of substrate) added Aliquat-336 (10 wt. % of substrate) in a single lot. The resulting reaction mixture was heated at 105±5 C, and the progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled to room temperature and quenched by adding water (25 ml). The resulting reaction mass was extracted with 3×30 ml ethyl acetate. Ethyl acetate layer washed twice with 20 ml of water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane system.

The synthetic route of 17600-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Waghmode, Suresh B.; Mahale, Ganesh; Patil, Viraj P.; Renalson, Kartik; Singh, Dharmendra; Synthetic Communications; vol. 43; 24; (2013); p. 3272 – 3280;,
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