Tag: M.W=100-200

Electric Literature of 1836-62-0,Some common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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.

A mixture of 4-(oxiran-2-ylmethoxy)-9H-carbazole (II) (25.0 g, 104.60 mmole) and 62.5 ml 2-propanol is heated to 70C to 80C. To this 2- (2- methoxyphenoxy) ethylamine (III) (25.33 g, 151.67 mmole) is added in one lot. The temperature of reaction mass is raised to reflux (80C to 85C) and maintained at this temperature for 2 hour. After that, this reaction mass is added to the pre-heated (80C to 85C) solution of L (+) tartaric acid (24. 32 g) (162.1 mmole) in 2-propanol (287.5 ml) and continued the reflux for next 1 hour, cooled to 50C to 55C and maintained for 1 hour. The product is filtered at the same temperature (50C to 55C) followed by three 33.5 ml wash with hot (50C to 55C) 2-Propanol. The wet product dried at 60C to 65C for 6-8 hours or till constant weight gave 33.0 g of Carvedilol tartarate (Yield = 56. 89%).

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

Reference:
Patent; CADILA HEALTHCAR LIMITED; WO2005/80329; (2005); A2;,
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Related Products of 658-89-9,Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, 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 mixture of o-phenylenediamine (1) and cyanoacetamide (2) were stirred in 200 C for 30 min without any solvent. After cooling, the mixture was dissolved in ethanol. The crude product was purified by silica gel column chromatography using dichloromethane-methanol (60:1) as eluant to give the pure compound 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethoxy)benzene-1,2-diamine, its application will become more common.

Reference:
Article; Pan, Ting; He, Xin; Chen, Bing; Chen, Hui; Geng, Guannan; Luo, Haihua; Zhang, Hui; Bai, Chuan; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 500 – 513;,
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Adding a certain compound to certain chemical reactions, such as: 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, 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 89282-70-2, SDS of cas: 89282-70-2

A solution of 2- { [5-bromo- 1 -(2-chlorophenyl)- 1 H-i ,2,4-triazol-3 -yl]methyl} -5-(4-chlorophenyl)-4- [(2S)-3 ,3,3 -trifluoro-2-hydroxypropyl] -2,4-dihydro-3H- 1 ,2,4-triazol-3 -one (Example 5A, 100mg, 173 jimol) in acetonitrile (330 jil) was treated with N,N-diisopropylethylamine (450 jil, 2.6mmol) and 2-methoxy-2-methylpropan-1-amine (178 mg, 1.73 mmol). The resulting mixture washeated for 5 h at 180C under microwave irradiation and evaporated. The residue was purified by preparative HPLC (Method 5) affording 82.5 mg (79% of th.) of the title compound.LC-MS (Method 2): R = 1.05 mm; MS (ESIpos): mlz = 600.2 [M+H]1H-NMR (400 MHz, DMSO-d6) [ppm]: 7.44 – 7.81 (m, 8H), 6.87 (d, 1H), 6.12 (t, 1H), 4.77 -4.93 (m, 2H), 4.29 (br ddd, 1H), 3.78 – 4.08 (m, 2H), 3.30 – 3.19 (m, 2H, overlapping with HDO peak), 3.06 (s, 3H), 1.05 (s, 6H).

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-Methoxy-2-methylpropan-1-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; (205 pag.)WO2019/81299; (2019); A1;,
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Electric Literature of 707-07-3,Some common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, molecular formula is C10H14O3, 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: 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.

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

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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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;,
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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;,
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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, Computed Properties of C7H10N2O

Step 3: 3~but-3-en~l-yl-8-rnethoxyquinoxalin-2-ol; To a solution of 3-methoxybenzene-l ,2-diamine from step 2 (5.6 g, 40.5 mmol) inDCE (250 ml), ethyl 2-oxohex-5-enoate (9.50 g, 60.8 mmol) was added, and the mixture was stirred at 60C for 14 hours. An additional charge of ethyl 2-oxohex-5-enoate (1.45 g, 9.28 mmol) was added, and the mixture was heated for 24 hours. The reaction mixture was concentrated and filtered from CH2CI2 to remove a portion of the undesired regio-isomer as a tan solid. The filtrate was purified by column chromatography on S1O2 (gradient elution, 1-9% acetone/C?Cl2) to give the title compound as a tan solid (6.4 g, 68.6 %) after triturating with 10% Et20/hexane. LCMS (ES+) m/z 231.1 (M+H)+.

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-Methoxybenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.R.L.; MCCAULEY, John, A.; LIVERTON, Nigel, J.; RUDD, Michael, T.; GILBERT, Kevin, F.; FERRARA, Marco; SUMMA, Vincenzo; CRESCENZI, Benedetta; WO2012/40040; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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 93919-56-3, category: ethers-buliding-blocks

Compound 25 (100 mg, 299.18 umol, 1.0 eq.), HATU (113.76 mg, 299.18 umol, 1.0 eq.) and triethylamine were dissolved in 2 mL of DCM in a 50 mL round-bottom flask. Compound B (114.38 mg, 598.36 umol, 2.0 eq.) was added and the reaction was kept at 25 C for 4 hours. LCMS detection reaction is complete. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by HPLC to give compound 8 as a white solid (80 mg, 157.67 umol, yield: 52.70%).

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; Shanghai Yaoming Kant, Immanuel New Drug Development Co., Ltd.; Wu Xiangyang; Wang Fei; Ao Zhiyong; Yang Kanghui; Wan Shuangyi; Wang Lijuan; (30 pag.)CN106478589; (2017); A;,
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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. 2216-69-5, name is 1-Methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2216-69-5

General procedure: 1mL [Bmim]NO3, 0.5 mmol substrate asshown in Scheme S1 and 0.25 mmolBr2 were added to a dried 45 mL tube equipped with a magneticstirring(note: the air in the tube was not removed). Then the reaction tube was sealed to perform the reaction for 24 h at 80 oC. Oncethe reaction time was reached, the mixture was cooled to room temperature and 3mL water was added. Then the desiredproduct was extracted with CH2Cl2 (3 ¡Á 10 mL). GC analysis of the mixture provided the GCyield of the product.

According to the analysis of related databases, 2216-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ren, Yun-Lai; Wang, Binyu; Tian, Xin-Zhe; Zhao, Shuang; Wang, Jianji; Tetrahedron Letters; vol. 56; 46; (2015); p. 6452 – 6455;,
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Electric Literature of 31576-51-9, These common heterocyclic compound, 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, 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 4-mercapto-4-nnethylpentanoic acid (226 pl_, 251 mg, 1 .69 mmol) in CHC were added 2-(2-methoxyethoxy)ethanamine (249 mI_, 242 mg, 2.03 mmol) and N-ethyl-N’-(3- dimethylaminopropyl)carbodiimide hydrochloride (0.35 g, 1 .82 mmol). The mixture was stirred for 1.5h, heated to 60 C for 2h and subsequently stirred at rt for 3d. The reaction mixture was then purified by silica chromatography (50% EtOAc in heptane EtOAc). The desired product was obtained as a colorless oil (0.23 g, 0.29 mmol, 54%). 1 H NMR (400 MHz, CDCI3) d (ppm) 6.20- 6.00 (bs, 1 H), 3.65-3.60 (m, 2H), 3.59-3.53 (m, 4fH), 3.49-3.44 (m, 2H), 3.40 (s, 3H), 2.40-2.33 (m, 2H), 1.96-1.88 (m, 2H), 1.63 (bs, 1 H), 1 .38 (d, J = 0.5 Hz, 6H).

Statistics shows that 2-(2-Methoxyethoxy)ethanamine is playing an increasingly important role. we look forward to future research findings about 31576-51-9.

Reference:
Patent; SYNAFFIX B.V.; VERKADE, Jorge Merijn Mathieu; HOOGENBOOM, Jorin; VAN BERKEL, Maria Antonia; VAN DELFT, Floris Louis; (95 pag.)WO2019/110725; (2019); A1;,
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