Author: Jessica.F

Application of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 mixture of the corresponding secondary amines 7a-d (0.77mmol), anhydrous K2CO3 (106.2mg, 0.77mmol) and KI (8.6mg, 0.052mmol) in CH3CN (10mL) were added the appropriate intermediates 2-4 (0.60mmol). The reaction mixture was warmed to 60-65C and stirred for 12-15h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (30mL) was added to the residue and the mixture was extracted with dichloromethane (30mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH as eluent, obtaining the corresponding 7-O-modified genistein derivatives.

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

Reference:
Article; Qiang, Xiaoming; Sang, Zhipei; Yuan, Wen; Li, Yan; Liu, Qiang; Bai, Ping; Shi, Yikun; Ang, Wei; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 314 – 331;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 1515-89-5, A common heterocyclic compound, 1515-89-5, name is 1-Bromo-3-(methoxymethyl)benzene, molecular formula is C8H9BrO, 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.

PREPARATION 103 3-Methoxymethylphenylboronic Acid Obtained as a yellow solid (100%), from 1-bromo-3-methoxymethylbenzene (J. Amer. Chem. Soc., 1989, 111, 6311; Tetrahedron 1985, 41, 1435) and trimethyl borate1 using the procedure of Preparation 101. delta(DMSOd6): 3.27 (s,3H), 4.38 (s,2H), 7.31 (m,2H), 7.68 (m,2H), 7.98 (brs,2H).

The synthetic route of 1515-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer INC; US6387931; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 645-36-3, name is 2,2-Diethoxyethanamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2,2-Diethoxyethanamine

A mixture of 2-bromo-5,6-dihydro-4H-pyrazolo[1,5-d][1,4]diazepine-7(8H)-thione (265.0 mg, 1.07 mmol), 2,2-diethoxyethan-1-amine(1.42 g, 10.7 mmol) and silver carbonate (590 mg, 2.14 mmol) in tetrahydrofuran (10 mL) was stirred at 80 C. for 1 h. The solvent was concentrated under vacuum. The residue was purified by reverse-phase column eluting with water (0.05% TFA)/CH3CN (85/15) to afford 2-bromo-N-(2,2-diethoxyethyl)-5,8-dihydro-4H-pyrazolo[1,5-d][1,4]diazepin-7-amine (295 mg, 80%) as a brown oil. LCMS (ESI) [M+H]+=345.0

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 18800-30-1 as follows. Formula: C8H8Br2O

To a solution of 1-bromo-4-(2-bromoethoxy)benzene (6, 1 g, 3.57 mmol), and 4-chloro-1H-pyrazole (439 mg, 4.2 mmol),, K2CO3 (985 mg, 7.14 mmol) and KI (29 mg, 0.17 mmol) were added and then heated at 80 C for 16 h. After completion, water (15 ml) was added into reaction mixture and the aqueous layer was extracted with ethyl acetate (2x15ml). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo to give 1-(2-(4-bromophenoxy)ethyl)-4-chloro-1H-pyrazole (7, 1.03 g, 83%) as white solid. 1H-NMR (400 MHz; CDCl3): d 4.26 (t, J = 5.0 Hz , 2H), 4.44 (t, J = 5.1 Hz , 2H), 6.74 (d, J = 8.9 Hz, 2H), 7.36 (d, J = 8.9 Hz, 2H), 7.44 (s, 1H), 7.51 (s, 1H).

According to the analysis of related databases, 18800-30-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; O’Brien, Alistair; Andrews, Stephen P.; Baig, Asma H.; Bortolato, Andrea; Brown, Alastair J.H.; Brown, Giles A.; Brown, Sue H.; Christopher, John A.; Congreve, Miles; Cooke, Robert M.; De Graaf, Chris; Errey, James C.; Fieldhouse, Charlotte; Jazayeri, Ali; Marshall, Fiona H.; Mason, Jonathan S.; Mobarec, Juan Carlos; Okrasa, Krzysztof; Steele, Kelly N.; Southall, Stacey M.; Teobald, Iryna; Watson, Steve P.; Weir, Malcolm; Bioorganic and Medicinal Chemistry Letters; vol. 29; 20; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 589-10-6 as follows. SDS of cas: 589-10-6

Example 101 N’-[1-imidazol-1-yl-1-[3-(2-phenoxyethoxy)thiophen-2-yl]methylidene]-N,N-dimethylhydrazine (compound No. 101) To a solution of methyl 3-hydroxythiophene-2-carboxylate (0.992 g, 6.27 mmol) in N,N-dimethylformamide (12 ml) were added beta-bromophenetole (1.268 g, 6.31 mmol) and potassium carbonate (1.059 g, 7.66 mmol), and the mixture was stirred at 80C for 4.5 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give methyl 3-(2-phenoxyethoxy)thiophene-2-carboxylate (1.624 g, 5.83 mmol, yield 93%).

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; EP2168951; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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: The corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl-oxycarbonyl) amino acids 20a-h (0.47 mmol) were dissolved in 50 mL of anhydrous CH2Cl2 and cooled to 0 C. 1-Hydroxybenzotriazole (HOBt) (0.7 mmol) and EDCI (0.56 mmol) were added, and the mixture was stirred for 30 min at 0 C. Subsequently, 0.39 mmol of compound 3 and finally 2.4 mL of N-ethyl diisopropylamine were added. The mixture was stirred for 16 h at ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flask-column chromatography (gradient elution with mixtures of chloroform/methanol) on silica gel as monitored by TLC. Synthesized target compounds 21a-h were characterized by mp, IR, ESR and HRMS analyses.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, its application will become more common.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-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. Quality Control of 4-Bromo-2-methoxyaniline

EXAMPLE 175B tert-butyl 4-bromo-2-methoxyphenylcarbamate A mixture of Example 175A (36.4 g, 180 mmol), and di-tert-butyl dicarbonate (47.2 g, 216 mmol) in THF (500 mL) was heated to reflux for 20 hours and cooled to ambient temperature. HPLC (using the conditions from Example 175A, product Rt=13.55 min and TLC (8:2 heptane/ethyl acetate, Rf of product=0.53, Rf of 4-bromo-2-methoxyaniline=0.27) indicated approximately 10% starting material was remaining. Additional di-tert-butyl dicarbonate (3.9 g, 18 mmol) was added and heating was continued for another 5 hours. The mixture was cooled and evaporated under reduced pressure. The residue was applied to a 400 gram silica gel column and eluted with 8:2 heptane/ethyl acetate. The fractions showing the desired product were combined and washed with saturated NaHCO3 and then brine. The organic solution was dried (MgSO4), filtered, and concentrated to provide 61.3 g of a mixture of the desired product and di-tert-butyl dicarbonate which was used directly in the next step.

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/43347; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 37466-89-0, name is 3-Methoxybenzene-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 37466-89-0, name: 3-Methoxybenzene-1,2-diamine

At room temperature, a solution of oxaldehyde in H20 (40%, 4 mL) was added to a solution of 3-methoxybenzene-1,2-diamine (3.66 g, 26.53 minol) in water (100.00 mL). Then NaHSO3 (7.59 g, 72.94 minol) was added slowly. The resulting solution was stirred for 15 min at room temperature. When the reaction was done, the insoluable solids in the reactionminxture were filtered out. The filtrate was extracted with DCM (300 mL x 3), and the organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 100% gradient) to yield 5-methoxyquinoxaline as dark red oil (3.02 g, 71%). MS: m/z = 161.0 [M+Hj.

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; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 2734-70-5, name is 2,6-Dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,6-Dimethoxyaniline

To a solution of 5-methylfuran-2-carboxylic acid (1.0 g, 8.0 mmol, 1 equiv) and 2,6- dimethoxyaniline (1.46 g, 9.5 mmol, 1.2 equiv) in DCM (10 mL) were added DMAP (44 mg, 0.4 mmol, 0.05 equiv) and EDCI (1.5 g, 9.6 mmol, 1.2 equiv) successively at room temperature. The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL), washed with water (3*20 mL) and brine (50 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by flash column chromatography (eluted with PE/EtOAc = 20/1 ~ 1/1) to afford the title compound N-(2,6-dimethoxyphenyl)-5-methylfuran-2-carboxamide as a white solid (1.23 g, 59 % yield). LC-MS: m/z 262.1 (M+H)+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2734-70-5.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 104197-14-0, 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 104197-14-0 as follows.

To a 200 mL flask which had been sufficiently dried under argon atmosphere, 30 mL of anhydrous pentane and 22.1 g (0.10 mol) of 4-bromo-2,6,-difluoroanisole were added and the mixture was cooled to -78 C. in a dry ice/acetone bath. Dropped thereto over 50 minutes was 61.2 mL of 1.6 mol/L n-butyl lithium hexane solution and the thus obtained mixture was subsequently stirred for 5 hours at -78 C. Thereto dropped over 30 minutes was 24.5 mL of 1 mol/L boron trichloride/hexane solution and the thus obtained reaction solution was stirred for 5 hours at -20 C. To this reaction solution, 80 mL of water was slowly added to hydrolyze the reaction mixture and the formed crystals were collected, which were then washed with 80 mL of hexane and 80 mL of water to obtain 13.0 g of tetrakis(3,5-difluoro-4-methoxyphenyl) lithium borate having an HPLC purity of 98.8% (Yield: 90%). The thus obtained product was subjected to measurements by 1H-NMR (heavy methanol solvent) and MALDI TOF-MS to confirm that it was the desired product. (Measurement Results)(1H-NMR (shift; ppm: multiplicity: number of protons)(3.8: s: 12) (6.5-6.6: m: 8)(0177)MALDI TOF-MS (m/z)mass: 583.25 (Theoretical value: 583.27)

According to the analysis of related databases, 104197-14-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Adeka Corporation; Kimura, Kentaro; Fujita, Shohei; Tamachi, Tomoya; US8383862; (2013); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem