Tag: M.W=100-200

Synthetic Route 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.

General procedure: At 0 C, a solution of 3(4)-bromobenzoyl chloride or 5-bromothiophene-2-carbonyl chloride (1 eq) in CH2Cl2 (2 ml/eq) was added drop wise to a solution of N-methylbenzylamine (1 eq) and triethylamine (1.15 eq) in CH2Cl2 (2 ml/eq). The mixture was kept stirred at 0 C for 3 h and evaporated under reduced pressure. The residue was purified by FC with n-hexane/ethyl acetate as eluant.

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:
Article; Xu, Kuiying; Al-Soud, Yaseen A.; Wetzel, Marie; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5978 – 5990;,
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Application of 1706-12-3, 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. 1706-12-3, name is 1-Methyl-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1(b) 4-(4-Methylphenoxy)benzenesulfonyl chloride {VIII-A: Z=CH3 } To a solution of 1.84 g (10.0 mmol) of 4-methyldiphenyl ether (J. Chem. Soc., Perkin Trans. 1; 1992, 407-408) with 2 mL of dichloromethane in an ice-bath was added a solution of chlorosulfonic acid (0.73 mL, 11.0 mmol) in 2 mL of dichloromethane dropwise. The resulting mixture was stirred at 0 C. to room temperature for 2 hours, and then oxalyl chloride (11.14 mL, 13.0 mmol) was added dropwise, followed by 0.15 mL of DMF. The resulting mixture was heated to 40 C. for 1 hour and then allowed to cool to room tempereature over a 2 hour period. The reaction mixture was poured into ice-pH 7 phosphate buffer (50 mL), then extracted with EtOAc:Hexane (4:3) (3*150 mL). The combined organic layers were washed with brine (75 mL). The aqueous layer was extracted with EtOAc/Hexane(4:3) (150 mL). The organic layer was dried over Na2 SO4, then evaporated by vacuum to give crude product as white solid. This solid was triturated with hexane and collected by filtration, then dried under high vacuum to give 1.555 g (57%) of 4-(4-methylphenoxy)benzenesulfonyl chloride as white solid: mp 295-300 C.; 1 H–NMR (DMSO-d6) delta 2.34 (s, 3H), 6.91-6.99 (dd, J=7.7,8.4 Hz, 4H), 7.24-7.27 (d, J=8.4 Hz, 2H), 7.61-7.63 (d, J=8.1 Hz, 2H). Anal. calc. for C13 H11 O3 SCI: C, 55.22; H, 3.92; S, 11.34; Cl, 12.71. Found: C, 55.06; H, 3.95; S, 11.28; Cl, 12.71.

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

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US5985900; (1999); A;,
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Synthetic Route of 592-55-2, 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 592-55-2 as follows.

To a solution of methyl 4-(hydroxymethyl)benzoate (500 mg, 3.0 mmol) and 2-bromoethyl ethyl ether (2.0 mL, 18 mmol) in dry DMF (25 mL) was added dropwise KHMDS (18 mL, 0.5 M in toluene, 9.0 mmol). After being stirred at 70 C was 2 h the mixture was treated with water and extracted with CH2Cl2. The combined organic layers were washed with brine and dried over MgSO4. After evaporation the crude product was purified by flash chromatography (hexane/EtOAc 5:1) to give 10a in 49% yield (350 mg). EI-MS: m/z 238 (M+); 1H NMR: (CDCl3, 600 MHz) delta (ppm): 1.23 (t, J = 7.0 Hz, 3H), 3.55 (q, J = 7.0 Hz, 2H), 3.61-3.67 (m, 4H), 3.91 (s, 3H), 4.64 (s, 2H), 7.42 (m, 2H), 8.01 (m, 2H); 13C NMR: (CDCl3, 90 MHz) delta (ppm): 15.2, 52.0, 66.7, 69.9, 69.9, 72.6, 127.2, 129.3, 129.7, 143.7, 167.0; IR: (NaCl) nu (cm-1): 2868, 1692, 1426, 1292, 1119, 764.

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huber, Daniela; Loeber, Stefan; Huebner, Harald; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 455 – 466;,
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Some common heterocyclic compound, 437-82-1, name is 2,6-Difluoroanisole, molecular formula is C7H6F2O, 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. Recommanded Product: 437-82-1

Example 37This example illustrates the preparation of compound 101a according to the approach provided in Scheme 31. The general method is applicable to other compounds of the present invention. In this example, Rv is H and Rw is CD3. Scheme 31Preparation of (5-bromo-2-chlorophenyl)(3,5-difluoro-4-hydroxyphenyl)- methanone (96)To a solution of 5-bromo-2-chlorobenzoic acid (3.2 g, 13.5 mmol) in dichloromethane (40 mL), oxalyl dichloride (1.7 mL, 27.1 mmol) was added. Then N, N-dimethylformamide (50 muL) was added dropwise. After the vigorous evolution of gas ceased, the mixture was stirred at 250C overnight prior to removal of the volatiles under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and cooled to 0 C. Aluminum trichloride (2.7 g, 20.4 mmol) was added in portions, and the mixture was stirred for 10 minutes. Then l,3-difluoro-2- methoxybenzene (2.0 g, 13.8 mmol) was added, and the mixture was stirred at 0 0C for 2 hours. Then the reaction was allowed to warm to 25 C overnight. The reaction was quenched with ice-water (30 mL) and extracted with dichloromethane (2 x 20 mL). The combined organic layers were washed with sodium hydroxide (2 M), water, hydrochloric acid (10%), and brine prior to drying over sodium sulfate. Crude product was obtained after dichloromethane was removed under reduced pressure. The sample was dissolved in tetrahydrofuran/methanol/water (30 mL, v/v/v = 2:3:1), and lithium hydroxide monohydrate (700 mg) was added. The mixture was stirred for 1 hour at 25 0C. The solvent was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3 x 30 mL), and the extracts were washed with brine, dried over sodium sulfate, and concentrated to a crude product under reduced pressure. The residue was purified by silica column chromatography to give 1.46 g of white solid (30% yield, purity: 95%). 1H-NMR (CDCl3, 400 MHz): delta 7.59-7.62 (m, IH), 7.49-7.50 (m, IH), 7.36-7.42 (m, 3H); HPLC-MS method: Method 2, retention time 3.81 min; MS ES” (m/z): 345(M – I)”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 437-82-1, its application will become more common.

Reference:
Patent; THERACOS, INC.; SEED, Brian; LV, Binhua; ROBERGE, Jacques, Y.; CHEN, Yuanwei; PENG, Kun; DONG, Jiajia; XU, Baihua; DU, Jiyan; ZHANG, Lili; TANG, Xinxing; XU, Ge; FENG, Yan; XU, Min; WO2010/9243; (2010); A1;,
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Electric Literature of 1077-01-6, A common heterocyclic compound, 1077-01-6, name is 1-Fluoro-3-(trifluoromethoxy)benzene, molecular formula is C7H4F4O, 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.

Under ice cooling mixture of 3-fluoro – trifluoromethoxyphenyl (20g) was dissolved in 40 ml of concentrated sulfuric acid, with rapid stirringWas added portionwise potassium nitrate (28g), was stirred at 0oC 3 hours and stirred at room temperature overnight, the reaction solution was carefullyGo on into 1 kg ice, stirred for 30 minutes, extracted with ethyl acetate, dried over sodium sulfate, filtered, and the filtrate was evaporated, the residue was purified by column chromatography to give 12 g pale yellow liquid.

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:
Patent; Shanghai Hansen Biological Pharmaceutical Co., Ltd.; Jiangsu Stockhausen Pharmaceutical Group Co., Ltd.; Sun, Xingyi; Wei, Mingsong; Cui, Yuanyuan; Tong, Chaolong; Zhang, Fujun; Bao, Rudi; Yu, Hongping; Xu, Yaochang; (41 pag.)CN105503827; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Product Details of 1535-73-5

General procedure: A mixture of B (1 mmol) and dichloromethane (10 ml) was stirred for 10 min, then EDCI (1.2 mmol) and HOBt (1.2 mmol) were added. Added the appropriate amine (1.2 mmol) into the mixed solution after 30 min and refluxed for 12 h. The reaction mixture was filtrated with water and then the filtrate was dried and evaporated. Purification by silica gel afforded C1-C27

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

Reference:
Article; Ni, Hai-Jun; Cheng, Hui-Jie; Ge, Wei-Wei; Lin, Meng-Xue; Li, Qing-Shan; Ruan, Ban-Feng; Letters in drug design and discovery; vol. 13; 6; (2016); p. 495 – 504;,
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Electric Literature of 54149-17-6, 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 54149-17-6 as follows.

To a solution of m-toluidine (lOg, 9.3mmol) in DMF (lOmL), 1-bromo-2-(2- methoxyethoxy)ethane (0.85g, 4.6mmol) and diisopropylamine (1.2g, 0.93mmol) was added. The mixture was heated to 100C for 4h. The mixture was diluted with ethyl acetate and water, and the layers were separated. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was then concentrated. The residue was purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (650mg, 66%) as an oil. ?H NMR (300 MHz, CDC13) oe 7.07 (t, J 7.5, 1H), 6.56 (d, J 7.5, 1H), 6.52 – 6.45 (m, 2H), 3.71 (t, J= 5.3, 2H), 3.67 – 3.62 (m, 2H), 3.60 – 3.52 (m, 2H), 3.31 (t, J= 5.3, 2H), 2.28 (s, 3H); ESI MS m/z 210 [M + Hj.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROMEGA CORPORATION; DUELLMAN, Sarah; ROBERS, Matthew, B.; WALKER, Joel, R.; ZHOU, Wenhui; ZIMPRICH, Chad; (230 pag.)WO2016/210294; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, 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 1017779-69-9, HPLC of Formula: C7H5F4NO

[0193j Step 1[0194j Corresponding amine (1 equiv.) and triethylamine (1.5 equiv.) was dissolved in CH2C12 (54 mM corresponding to amine) and stirred at -78 C. Triphosgene (0.45 equiv.) dissolved in CH2C12 (20 mM, corresponding triphosgene) was added dropwise at -78 C. The reaction was then warm to rt and was stirred for 30 mm. The reaction was cooled to 0 C. Corresponding piperidine (1.5 equiv.) and triethylamine (1.5 equiv.) dissolved in CH2C12 (54 mM, corresponding piperidine) was added slowly and the reaction was further stirred at rt for 12 h. The reaction was quenched with the addition of HC1 solution (2M). The organic layer was collected and the aqueous layer was further extracted with EtOAc (EtOAc: Aqueous layer 1:1) for three times. The combined organic layer was washed with sat. NaC1 solution. The organic layer was dried over anhydrous magnesium sulfate and was concentrated in vacuo. The product was used without further purification.[0277j The reaction was carried out according to synthetic pathway 2. The 3-fluoro-4- (trifluoromethoxy)aniline (109 mg, 559 jimol) was reacted with 1-(4-aminopiperidin-1-yl)-2- methylpropan-1-one (143 mg, 838 jimol). The product was purified by flash chromatography using ethyl acetate :hexane (7:3). The product was further purified by recrystallization using methanol and water.[0278j Yield: 150 mg, 383 jimol, 68.6% yield. Purity (H-NMR): 95%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; EICOSIS, LLC; HAMMOCK, Bruce, D.; LEE, Kin, Sing, Stephen; INCEOGLU, Ahmet, Bora; WO2015/148954; (2015); A1;,
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Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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. category: ethers-buliding-blocks

3,3-diethoxypropan-1-amine (6 g, 40.76 mmol, 1.00 equiv) was dissolved in 1,4- dioxane (30 mL) in the presence of TEA (4.45 g, 43.98 mmol, 1.08 equiv), then cooled to0C. (Boc)20 (9.6 g, 43.99 mmol, 1.08 equiv) diluted in 20 mL of 1,4-dioxane was added drop-wise. The solution was agitated 2 hours at 0C then overnight at ambient temperature before being neutralised with 10 mL of water. The pH was adjusted to 5 with HC1 (1 %). The solution was extracted 3 times with 50 mL of EtOAc. The organic phases were combined, dried over sodium sulfate, filtered and concentrated to yield 8.21 g (81 %) of compound 1ZDin the form of a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41365-75-7, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; JOUHANNEAUD, Alexandra; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; CHAMPION, Thierry; ROBERT, Alain; HAEUW, Jean-Francois; RILATT, Ian; PEREZ, Michel; (244 pag.)WO2017/72196; (2017); A1;,
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Related Products of 126-38-5,Some common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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 solution of 3j (0.360?g, 2.00?mmol) and 1-bromo-2,4-dimethoxypropane (11, 0.330?mL, 2.44?mmol) in acetic acid (4.0?mL) was stirred at reflux for 3?h. After the solution was cooled to room temperature and concentrated, it was diluted with EtOAc and washed with water and saturated NaHCO3(aq). The organic layer was dried over MgSO4(s), filtered, and concentrated to afford a residue, which was purified by Isco Combi-Flash Companion column chromatography (0-20% EtOAc in n-hexane) to give 12 (0.114?g, 26%) as a yellow solid. 1H NMR (CDCl3, 300?MHz) delta 7.57 (d, 1H), 7.27-7.20 (m, 2H), 7.11 (dd, 1H), 7.05 (br s, 1H), 6.13 (s, 1H), 2.66 (q, 2H), 2.28 (s, 3H), 1.23 (t, 3H); 13C NMR (CDCl3, 75?MHz) delta 167.32, 148.57, 138.25, 136.07, 129.23, 127.04, 125.08, 121.85, 101.53, 24.32, 17.23, 14.25; HPLC Purity?=?100%, tR?=?29.20?min; LC-MS (ESI) m/z: 219.0 [M + H]+; HRMS (ESI): m/z calculated for C12H15N2S [M + H]+: 219.0956 Found: 219.0950.

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

Reference:
Article; Lin, Shu-Yu; Kuo, Yu-Hsien; Tien, Ya-Wen; Ke, Yi-Yu; Chang, Wan-Ting; Chang, Hsiao-Fu; Ou, Li-Chin; Law, Ping-Yee; Xi, Jing-Hua; Tao, Pao-Luh; Loh, Horace H.; Chao, Yu-Sheng; Shih, Chuan; Chen, Chiung-Tong; Yeh, Shiu-Hwa; Ueng, Shau-Hua; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 312 – 323;,
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