Tag: M.W=100-200

Electric Literature of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 8-bromo-6-chloroimidazo[l,2-b]pyridazine-3-carbonitrile (2.82 g, 13.23 mmol), l-(4-methoxyphenyl)-N-methylmethanamine (2.00 g, 13.23 mmol) and diisopropylethylamine (4.62 mL, 26.5 mmol) in tetrahydrofuran (25 mL) was heated to 60 °C for 3 hours and then concentrated to dryness. The crude product was triturated with methanol and filtered rinsing with methanol. The solid was dried and collected as is (3.85 g, 89percent yield). NMR (400MHz, CHLOROFORM-d) delta 7.99 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.93 – 6.82 (m, 2H), 6.12 (s, 1H), 5.45 (br. s., 2H), 3.80 (s, 3H), 3.20 (br. s., 3H). LC retention time 1.05 min [J]. MS (E+) m/z: 328 (MH+).

The chemical industry reduces the impact on the environment during synthesis 4-Methoxy-N-methylbenzylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
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Synthetic Route of 103-50-4, 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 103-50-4 as follows.

General procedure: To a test tube charged with CuCl (2.0 mg, 0.02 mmol) andisochroman (1a; 251 muL, 2.0 mmol) in t-BuOH (20 mL) wasadded TBHP (5.0-6.0 M in decane, 10.9 muL, 0.6 mmol) and themixture was stirred and heated at 50 C for 12 h under open air.After cooling to room temperature, the reaction was quenchedwith 25% aqueous ammonia solution and water then themixture was extracted with EtOAc. The separated organic layerwas dried over Na2SO4 and products were concentrated after filtration.The residue was purified by silica gel column chromatography(EtOAc/hexane, 1:10) to give isochromanone (2a) as acolorless oil in 83% yield.

According to the analysis of related databases, 103-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanaka, Hirotaka; Oisaki, Kounosuke; Kanai, Motomu; Synlett; vol. 28; 13; (2017); p. 1576 – 1580;,
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Synthetic Route of 52189-63-6,Some common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, molecular formula is C8H9FO2, 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.

Example 53 3- {4- [3-Fluoro-5- (2-phenoxy-4-trifluoromethyl-phenoxy)-phenoxy]-2-methyl-phenyl}- propionic acid Step A 3-Fluoro-5-methoxy-phenol A-78 C solution of l-fluoro-3, 5-dimethoxybenzene (4. 98 g, 31.9 mmol) in dry CH2C12 (50 mL) is treated with a 1 M CH2C12 solution of boron tribromide (128 mL, 128 mmol), and the mixture is warmed to 0 C and stirred under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 2.40 g (53%) of the title compound. Rf= 0.49 (1/1 hexanes/EtOAc).’H NMR (400 MHz, CDCl3). MS (ES-) m/z mass calculated for C7H702F 142, found 141 (M-1,100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37763; (2005); A1;,
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Reference of 36865-41-5, These common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, 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 stirred solution of [2], X=Br (1 wt, 1 mol eq.) in DMF (5 vol.) was added (0229) portionwise CS2CO3 (2.34 wt, 1.5 mol eq.) at room temperature, and then the reaction mixture was continued on stirring for 10 min. Then, l-bromo-3-methoxypropane (0.65 wt, 1.2 mol eq.) was added dropwise to the reaction mixture at room temperature and stirred for 16 h at the same temperature. The reaction was monitored by TLC. After completion of reaction, the resultant reaction mixture was diluted with water (3.2 vol.), and stirring was continued for 30 min to produce the solid, which was filtered, washed with water and dried under reduced pressure to obtain the product 5-bromo-2-chloro-3-(3-methoxypropoxy)pyridine [3], X=Br as off-white solid. 1H-NMR [300MHz, DMSO-d6]: d 8.10 (d, 1H, J= 1.5 Hz), 7.87 (d, 1H, J= 1.5 Hz), 4.15 (t, 2H, J= 6.0 Hz), 3.45(t, 2H, J= 6.4 Hz), 3.22 (s, 3H), 1.95 (quint, 2H, 7=6.4, 12.4 Hz).

Statistics shows that 1-Bromo-3-methoxypropane is playing an increasingly important role. we look forward to future research findings about 36865-41-5.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; CHEN, Shuai; DORSEY, Bruce D.; GOTCHEV, Dimitar B.; NGUYEN, Duyan; PALLERLA, Mahesh Kumar; PAMULAPATI, Ganapati Reddy; (76 pag.)WO2019/200109; (2019); A1;,
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Electric Literature of 19500-02-8, The chemical industry reduces the impact on the environment during synthesis 19500-02-8, name is 3-Methoxy-2-methylaniline, I believe this compound will play a more active role in future production and life.

The imidate salt 2g2 (1.5g, 7.65mmol) was combined with 2-methyl-3-aminoanisole 2a2 (1.05g, 7.65mmol, 1 eq.) in ethanol (15 ml) under an N2atmosphere. The reaction mixture was stirred at R.T. (24 h) and monitored by HPLC.The reaction mixture was concentrated and then ether was added and the mixturefiltered. The solids were washed with ether and the combined ether washesconcentrated in vacuo. The resulting adduct 2m1 was purified by chromatography(SiO2, 15percent EtOAc/hexanes) to obtain as a yellow oil (2.11g, 99percent). MS electrospray:(M + H)+; 280 and (M – H)-; 278.

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-Methoxy-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
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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., Application In Synthesis of (Trimethoxymethyl)benzene

General procedure: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

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; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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767-91-9, name is 2′-Methoxyphenyl acetylene, 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. COA of Formula: C9H8O

General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong, Qizhi; Li, Ningbo; Qiu, Renhua; Wang, Jinying; Guo, Cancheng; Xu, Xinhua; Journal of Organometallic Chemistry; vol. 799-800; (2015); p. 122 – 127;,
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These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-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. category: ethers-buliding-blocks

To a stirred light brown solution of 10.0 g (49.6 mmol) 3-Fluoro-4-methoxy aniline in 56 ml DCM was added rapidly a solution of 4.38 g (52 mmol, 1.05 eq.) NaHCO3 in 70 ml of water. To the resulting biphasic mixture was added under vigorous stirring 5.72 ml (74.4 mmol, 1.5 eq.) methyl chloroformate over a period of 30 min. The light brown reaction mixture was stirred for 1.5h at RT. The organic phase was separated and washed twice with a total amount of 50 ml water, and the combined aqueous phases were washed twice with a total amount of 100 ml DCM. The combined organic phases were dried over 2 g Na2SO4 and filtered with suction on a funnel with a fritted disk. The cake was washed in total with 50 ml DCM. The DCM was partially removed under reduced pressure to about 1/3 of its original volume and then 70 ml heptane was added dropwise under stirring within 30 min, whereby the product precipitated. From this suspension, DCM was completely removed under reduced pressure. Finally, the suspension was stirred in an ice bath for 1h, the crystals were filtered off with suction on a funnel with a fritted disk and washed with three 10 ml portions, in total with 30 ml ice cold heptane. The wet off-white crystals were dried at 50°C in vacuo to yield 9.65 g (97.7percent of theory) of the title compound as off-white crystals (m.p. = 96.1-96.5°C) 1H-NMR data (CDCl3, 300 MHz): delta 7.29 (m, 1H), 6.98 (m, 1H,), 6.89 (dd, 1H), 6.44 (br s, 1H), 3.86 (s, 3H), 3.77 (s, 3H). MS m/e (percent): 200 ([M+H]+, 100).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. Hoffmann-La Roche AG; EP2011783; (2009); A1;,
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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, Recommanded Product: 89282-70-2

A mixture of phenyl 5-({trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}carbamoyl)-1 H-imidazole-4-carboxylate (150 mg, 0.309 mmol,) and 2-methoxy-2-methylpropan-1 -amine(160 mg, 1.55 mmol, GAS No 89282-70-2) in tetrahydrofuran (4.8 ml) was stirred at 600over night. For work-up, the reaction mixture was concentrated and the residue was purified by flash chromatography (25 g Snap Cartridge, ethyl acetate/ethanol gradient, 0% -> 5% ethanol) to yield the title compound (18.0 mg, 12 yield).[C-MS (Method 6): R = 1 .08 mm; MS (ESIpos) m/z = 494.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 13.20-12.45 (m, 1H), 11.43-1 0.70 (m, 1H), 9.52 (s,1H), 8.69-7.89 (m, 1H), 7.82 (s, 1H), 7.65-7.57 (m, 1H), 7.53-7.47 (m, 1H), 7.27-7.18 (m,1H), 3.89-3.66 (m, 1H), 3.37 (d, 2H), 3.15 (s, 3H), 2.48-2.38 (m, 1H), 2.10-1.75 (m, 4H),1.71 -1 .32 (m, 4H), 1.14 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methoxy-2-methylpropan-1-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Application of 1159512-64-7,Some common heterocyclic compound, 1159512-64-7, name is 2-Fluoro-3-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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 (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (1 equiv) in DMF (10 vol) at 0 C. under nitrogen atmosphere was added 2-fluoro-3-(trifluoromethoxy)aniline (1.2 equiv), HBTU (1.5 equiv) and DIPEA (3 equiv). The reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, the reaction mixture was quenched with water. The resulting mixture was extracted with DCM. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and then concentrated. The residue was purified by column chromatography on silica gel using DCM/MeOH to give compound 1239.

The synthetic route of 1159512-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
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