Month: March 2021

Reference of 16618-68-1, These common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-methoxyaniline, 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.

In 50 ml by adding three-necked bottle 1.01g3-methoxy-5-bromoaniline(5mmol), 1.40g (5.5mmol) connecting boric acid frequency ester, 1.47g (15mmol) and potassium acetate PdCl2(dppf) catalyst (150 mg), vacuum pumping and nitrogen injection 6 times, the state of the protection of nitrogen by adding DMSO (25 ml), 80 C reaction 18h, in a water cooling retrodisplacement, precipitate after filtering, washing, drying to obtain the crude column chromatography separation (petroleum ether: ethyl acetate = 1:5) shall be 1.03g yellow powdery solid, yield 82.4%.The 0.99g the above-mentioned preparation of the compound (4mmol) by adding 100 ml round-bottom flask, add 30 ml of methanol is dissolved, add 0.56gNH4Cl (10mmol), constant voltage dropping funnel for slowly dripping 2.56gNaIO4(12mmol) of 7 ml aqueous solution, stirring the mixture at room temperature for reaction 18h, TLC detection, filtering to remove the inorganic salt, methanol filters after evaporation to dryness, drying to obtain the crude product purification column chromatography (petroleum ether: ethyl acetate = 1:5) shall be near white powdery solid 0.53g, yield 79.1%.

The synthetic route of 16618-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ocean University of China; Jiang, Tao; Yin, ruijuan; Zhang, Li Juan; (38 pag.)CN103497211; (2016); B;,
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Electric Literature of 702-24-9, A common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, molecular formula is C9H13NO, 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.

A mixture of 3-(3-amino-4-fluorophenyl)-7-chloro-1-isopropyl-1,6-naphthyridin-2(1H)-one (4 g, 12.1 mmol) and (4-methoxybenzyl)methylamine (15 mL) was degassedunder reduced pressure, then heated to 180C under N2 for 4 h. After cooling, the reactionmixture was diluted with Et20. The precipitate was filtered, washed with Et20 and dried invacuo to giVe 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-[( 4-methoxybenzyl)-methylamino]-1H-[1,6]naphthyridin-2-one (5.3 g) as a solid contaminated with (4-methoxybenzyl)methylamine HCl salt.

The synthetic route of 702-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); A1;,
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Electric Literature of 7664-66-6, 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. 7664-66-6 name is 4-Isopropoxyaniline, 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.

The compound obtained in Step 5 (19 mg) was dissolved in dioxane (1 mL), 4 isopropoxyphenylaniline (12mg) and 4N hydrochloric acid dioxane (64muL), and the mixture was stirred for 20 minutes in a microwave irradiation under 180 . The reaction solution was extracted three times with chloroform after adding a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was concentrated after dried over sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (13mg, 57%).

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

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
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Synthetic Route of 910251-11-5, 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. 910251-11-5 name is Potassium trifluoro(methoxymethyl)borate, 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.

4-Chloro-2-(4-chlorophenyl)-N-[3-(lH-imidazol-2-yl)propyl]quinazoline-7-carboxamide (200 mg, 0.0005 mol)(INT-5 described in Example 7), potassiummethoxymethyltrifluoroborate (214 mg, 0.00141 mol) dicesium carbonate (458 mg, 0.00141 mol) and SiliaCat DPP-Pd(0.260 mmol/g loading; 361 mg, 0.0000938 mol) were weighed into a 2-5mL microwave vial purged with nitrogen 5 min then added 1,4-dioxane (7.65 mL, 0.0980 mol) and water (1.69 mL, 0.0938 mol). The mixture was heated at 155 C for 80 min under microwave irradiation. After cooling, the reaction mixture was poured into EtOAc and water. The layers were separated and the aqueous layer was extracted two more times with EtOAc. The combined organic layer was dried over anhydrous MgSC>4 and concentrated in vacuo, and purified by HPLC to give 2-(4-chlorophenyl)-N-[3-(lH-imidazol-2-yl)propyl]-4- (methoxymethyl)quinazoline-7-carboxamide (20.0 mg, 10%) as a white solid. LCMS (ESI+): m/z = 436.2 (M+H). lH NMR (400 MHz, DMSO-dg) delta 9.12 (s, 1H), 8.63 – 8.56 (m, 3H), 8.45 (d, J= 8.6 Hz, 1H), 8.16 (s, 1H), 8.13 (d, J= 8.7 Hz, 1H), 7.68 (d, J= 8.6 Hz, 2H), 6.91 (s, 2H), 5.13 (s, 2H), 3.48 (s, 3H), 3.32-3.44 (m, 2H), 2.73 (t, J = 7.5 Hz, 2H), 2.01 – 1.93 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium trifluoro(methoxymethyl)borate, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; FREEZE, Brian, Scott; GIGSTAD, Kenneth, M.; JANOWICK, David, A.; LEE, Hong, Myung; SHI, Zhan; SOUCY, Francois; VYSKOCIL, Stepan; (237 pag.)WO2016/118565; (2016); A1;,
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Reference of 150-78-7, 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. 150-78-7, name is 1,4-Dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,4- dimethoxybenzene Q-8 (7.5 g, 53.57 mmol) in acetic acid (25 mL) was added a solution of bromine (17.4 g, 108.9 mmol) in acetic acid (5 mL) at room temperature. After stirring for 2h, the solution was cooled to 10 0C. The resulting fine precipitate was filtered, washed with water (20 mL), and dried under vacuum to obtain compound Q-9 (1Og, 63%) as a white solid. TLC Rf = 0.5 (petroleum ether – EtOAc, 9.9:0.1); 1H NMR (CDCl3) delta 7.10 (s, 2H), 3.84 (s, 6H).

The synthetic route of 1,4-Dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; DJABALLAH, Hakim; ANTCZAK, Christophe; WO2010/129049; (2010); A1;,
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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-4-phenoxybenzene

General procedure: The chemical synthesis was started with chlorosulfonylationof the substituted benzenes (S1) individually in dry chloroformby dropwise addition of chlorosulfonic acid over a period of45-60 mins at 0-5 C. After completion of chlorosulfonic acid addition,the reaction mixture was stirred for additional 45 min atroom temperature and the mixture was poured over crushed ice.The mixture was extracted thrice with 50 ml chloroform whichwas dried overnight in presence of anhydrous sodium sulfate. Afterevaporation of the solvent chloroform, substituted benzenesulfonylchlorides (I1) were obtained individually in solid formswhich were used for next step without any purification.

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:
Article; Adhikari, Nilanjan; Halder, Amit K.; Mallick, Sumana; Saha, Achintya; Saha, Kishna D.; Jha, Tarun; Bioorganic and Medicinal Chemistry; vol. 24; 18; (2016); p. 4291 – 4309;,
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Synthetic Route of 944561-44-8, 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. 944561-44-8, name is 2-[2-(2-Propynyloxy)ethoxy]ethylamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of compound 7 (200 mg, 0.34 mmol) and terminalalkynyl substituted amine (0.43 mmol) in DMF (10 mL), Na2CO3(72 mg, 0.68 mmol) was added. The resulting solution was vigorouslystirred for 24 h at 60 C. The solvent was removed bysteaming. The residue was purified by column chromatography.

The chemical industry reduces the impact on the environment during synthesis 2-[2-(2-Propynyloxy)ethoxy]ethylamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liang, Shuobin; Li, Man; Yu, Xiaojuan; Jin, Hongwei; Zhang, Yongmin; Zhang, Lihe; Zhou, Demin; Xiao, Sulong; European Journal of Medicinal Chemistry; vol. 166; (2019); p. 328 – 338;,
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Synthetic Route of 111-95-5, The chemical industry reduces the impact on the environment during synthesis 111-95-5, name is Bis(2-methoxyethyl)amine, I believe this compound will play a more active role in future production and life.

To a stirred solution of DCM, bis(2-methoxyethyl)ami?e (40.0 g, 44.0 ml_, 300 mmol), and triethylamine (69.25 ml_, 500 mmol), under a nitrogen atmosphere at -78 0C was added drop wise bromo acetyl bromide (34.8 ml_, 400 mmol). After stirring at -78 0C for 5 h, the reaction mixture was allowed to warm up to -20 0C and then quenched by addition of water (60 ml_). The organic phase was washed with distilled water (3 x 30 ml_), saturated ammonium chloride (3 x 30 ml_), saturated sodium bicarbonate (3 x 30 ml_) and brine (2 x 30 ml_). The organic phase was then dried over magnesium sulfate, filtered and solvents removed via rotary evaporation to yield a crude product in 82 % yield (62.3 g, 245 mmol). The crude product was then distilled under high vacuum at 170 C to give pale yellow crystals in 49 % yield (35.57 g, 140 mmol). Pure product can also be recrystallised from the crude material with diethyl ether.1H delta ppm 4.02 (s, 2H), 3.66 (t, J = 5.2 Hz, 2H), 3.55 (br, 3H), 3.53 (t, J = 5.0 Hz, 3H), 3.33 (s, 6H)13C delta ppm 167.79, 70.74, 70.27, 59.13, 58.94, 50.12, 46.90, 27.20

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUBLIN CITY UNIVERSITY; WO2009/24607; (2009); A1;,
Ether – Wikipedia,
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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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (Trimethoxymethyl)benzene

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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Related Products of 123652-95-9, 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. 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00326] To a solution of compound 15 (2.3 g, 13.5 mmol) in SOd2 ( 20 mL) was refluxed for 4h, The mixture was concentrated and then re-dissolved in DCM (5 mL) and transfeffed to a solution of the amine 2 ( 2.7 g 17.6 mmol) and TEA (4.0 g, 40.5 mmol). The mixture was stirred at rt for 3 h. The resulting mixture was purified by FCC (PE/EA=3:1) to afford the product 16 (3.lg, 75.3%). ?H NMR (400 MHz, CDC13): 8.19 (d, J =4.8 Hz, 1H), 7.11-7.06 (m, 3H), 6.92(t, J = 8.8 Hz, 1H), 6.32-6.28 (m, 1H), 4.55 (d, J = 6.0 Hz, 2H), 3.87 (s, 3H), 2.34 (s, 3H); mlz (ESI+) (M+H)+ = 309.00.

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, (3-Fluoro-4-methoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; YANG, Wenjin; CHEN, Che-Hong; MOCHLY-ROSEN, Daria; WO2014/160185; (2014); A2;,
Ether – Wikipedia,
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