Month: August 2021

Application of 179022-43-6, The chemical industry reduces the impact on the environment during synthesis 179022-43-6, name is Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, I believe this compound will play a more active role in future production and life.

Example 3: 8- [7-(cis-4-methyl-cyclohexyloxy)-8-trifluoromethyl-naphthalen-2-ylmethyl]-8-aza-bicyc lo[3.2.1]octane-3-carboxylic acid To a solution of methanesulfonic acid 7- (cis-4-methyl-cyclohexyloxy)-8-trifluoromethyl-naphthalen-2-ylmethyl ester (105 mg, 0.252 mmol) in N,N-dimethylformamide (2.9 mL, 38 mmol), 8- aza-bicyclo[3.2.1]octane-3-carboxylic acid methyl ester; HC1 salt (103.72 mg, 0.50426 mmol) was added, followed by cesium carbonate (246.44 mg, 0.75638 mmol). The reaction was then heated at 80 C for lh. LCMS showed no SM left, and the completion of the reaction (RT 1.56 min.; MH+ 490.3 and 1.49 min, 476.30. Cooled down, the reaction mixture was diluted with EtOAc, washed with water (2x). The organic phase was then separated, dried and concentrated. The crude was purified by HPLC, removed the solvent, the ester was then dissolved in tetrahydrofuran (1.2 mL, 14 mmol) , treated with 1.0 M of lithium hydroxide in water(1.8 mL, 1.8 mmol) at rt overnight. Acidified with conc.HCl, the organic layer was dried and concentrated. The crude was then purified by HLPC to give the title compound as a white powder (57.6 mg, 48%). LCMS: RT = 1.49 min.; MH+ 476.20; 1H NMR (400 MHz, METHANOL-d4) delta 8.36 (s, 1H), 8.15 (d, J = 9.29 Hz, 1H), 8.04 (d, J = 8.34 Hz, 1H), 7.61 (d, J = 9.54 Hz, 1H), 7.57 (d, J = 6.78 Hz, 1H), 4.96 (br. s., 1H), 4.41 (s, 2H), 4.02 (br. s., 2H), 2.81 – 3.09 (m, 2H), 1.44 – 2.63 (m, 16H), 0.98 (d, J = 5.84 Hz, 3H).

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, Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; MI, Sha; PENG, Hairuo; SHAO, Zhaohui; SUN, Lihong; TAVERAS, Arthur; WANG, Deping; XIN, Zhili; ZHANG, Lei; WO2014/18881; (2014); A1;,
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Synthetic Route of 50413-30-4, 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 50413-30-4 as follows.

a) 4-((3,4-Difluorophenyl) amino) -7-fluoro-1H-indole-2-carboxylic acid ethyl ester 4-Bromo-7-fluoro-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.7 mmol) was dissolved in toluene (15 mL), and Pd2 (dba) 3 (64 mg, 0.07 mmol) and Davephos (55 mg) were sequentially added. , 0.14 mmol) and K3PO4 (446 mg, 2.1 mmol, 2.1 mL of H2O). After stirring well, a solution of 3,4-difluoroaniline (271 mg, 2.1 mmol) in toluene (4 mL) was added, and the reaction was refluxed for 20 h under the protection of argon. Cool to room temperature, concentrate, add EA (30mL) to dissolve the residue, 5N hydrochloric acid (10mL × 2), saturated brine (20mL × 2), water (20mL × 2) extraction, column chromatography (P / E = 5: 1) 177 mg of white solid was obtained with a yield of 75.7% and melting point: 195-197 C.

According to the analysis of related databases, 50413-30-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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Synthetic Route of 2876-78-0, 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. 2876-78-0, name is Methyl 1-Naphthaleneacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1): EPO In Scheme (1), compound 2 was prepared from compound 1 in 33% yield according to reference paper “J. Amer. Chem. Soc, 1935, 57, 1658-1659”, the relevant teachings of which are incorporated herein by reference. Conversion of compound 2 in the presence of dimethyl sulphate and potassium carbonate in acetone gave compound 3 in 96% yield after chromatography on silica gel. Compound 4 was prepared by coupling of compound 3 with methyl naphthalene acetate using sodium methoxide as base. The isolation yield is 29%. Proton NMR of compound 4 indicated equilibrium between /3-keto and enolate.Compound 4 (90 mg) was treated with BBr3 (20 equiv.) in DCM. Purification of the crude by chromatography gave compound 5 as pink solid (46 mg).Preparation of compound 6 was conducted using compound 5 (30 mg) in the presence of 0.20 mL of hydrazine (45 equiv) in DME (2 mL) at reflux 2 hours. Chromatography of the crude product gave compound 6 as a light purple solid (25 mg, 74% yield). 1H-NMR (Acetone-d6) delta (ppm): 7.89 (t, J=7.8Hz, 2H), 7.74 (d, J=7.8Hz, IH), 7.3-7.5 (m, 4H), 6.42 (s, IH), 6.34(s, IH), 1.9 (m, 2H), 0.32 (t, J=7.5Hz, 2H); ESMS calcd. for C21H18N2O3: 346.1; Found: 347.6 (M+l)+.

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, Methyl 1-Naphthaleneacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/21966; (2007); 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., Application In Synthesis of Diethyl 2-bromo-2-methylmalonate

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Application of 52449-43-1, The chemical industry reduces the impact on the environment during synthesis 52449-43-1, name is Methyl 4-chlorophenylacetate, I believe this compound will play a more active role in future production and life.

Example 1 Preparation of Methyl 2-bromo-(4-Chlorophenyl)acetate 116 g (0.585 mol) of 1,3-dibromo-5,5-dimethylhyntantoin [sic] and 1 g of AIBN were added portionwise to the solution of 215.3 g (1.17 mol) of methyl 4-chlorophenylacetate in 500 ml of tetrachloromethane, and the mixture was refluxed for 24 hours. This was followed by washing with water and 1 N sodium hydroxide solution, the aqueous phases were extracted with methylene chloride, and the organic phases were dried and concentrated. This gave 260 g of the title compound. 1H NMR [delta, (CDCl3)]: 3.8 (s, 3H); 5.3 (s, 1H).

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, Methyl 4-chlorophenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Grammenos, Wassilios; Sauter, Hubert; Cullmann, Oliver; Gewehr, Markus; Muller, Bernd; Blasco, Jordi Tormo i; Gotz, Norbert; Volk, Thorsten; Lorenz, Gisela; Ammermann, Eberhard; Stierl, Reinhard; Strathman, Siegfried; US2003/191190; (2003); A1;,
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Electric Literature of 6065-82-3, 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. 6065-82-3 name is Ethyl diethoxyacetate, 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 magnesium turnings (270 mg, 11.1 mmol) were dried in vacuo by heating with a heat gun. After cooling to room temperature and being placed under an argon atmosphere, THF (17.5 mL) was added thereto, followed by slow addition of 3-(tert-Butyldimethylsilyloxy)benzyl chloride (102) (2.57 g, 10.0 mmol) at room temperature. The reaction mixture was warmed as the result of an exothermic reaction and most of the magnesium turnings were consumed. After cooling to room temperature, it was used directly in the next reaction as a THF solution of 3-(tert-butyldimethylsilyloxy)benzylmagnesium chloride (103) was cooled to room temperature and was used as it was in the next reaction. (0404) Under an argon atmosphere, to a solution of ethyl diethoxyacetate (1.80 mL, 10.1 mmol) in THF (20 mL) was added slowly a THF solution of (103) prepared above at -78 C. After stirring at -78 C. for an hour, to this was added 20% aqueous solution of ammonium chloride (30 mL) and the product was extracted with ethyl acetate (×3). The organic layer was sequentially washed with water (×1) and saturated brine (×1), and dried over anhydrous sodium sulfate. After filtration, the mixture was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=10/1) to give 3-[3-(tert-butyldimethylsilyloxy]phenyl]-1,1-diethoxypropan-2-one (104) as a colorless oily substance (1.90 g, 5.39 mmol, 53.9%). (0405) TLC Rf=0.48 (n-hexane/ethyl acetate=10/1); (0406) 1H NMR. (400 MHz, CDCl3) delta 0.19 (s, 6H), 0.97 (s, 9H), 1.25 (t, 6H, J=7.0 Hz), 3.54 (dq, 2H, J=9.5, 7.0 Hz), 3.69 (dq, 2H, J=9.5, 7.0 Hz), 3.82 (s, 2H), 4.63 (s, 1H), 6.68-6.75 (m, 2H), 6.81 (d, 1H, J=7.8 Hz), 7.16 (dd, 1H, J=7.8, 7.8 Hz); (0407) 13C NMR (67.8 MHz, CDCl3) delta -4.4 (2C), 15.2 (2C), 18.2, 25.7 (3C), 43.7, 63.3 (2C), 102.2, 118.5, 121.6, 122.8, 129.3, 135.2, 155.7, 202.9; (0408) IR (KBr, cm-1) 781, 839, 982, 1063, 1157, 1275, 1487, 1585, 1601, 1736, 2859, 2886, 2930, 2955, 2974; (0409) HRMS (EI) m/z 352.2073 (M, C19H32O4Si required 352.2070).

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

Reference:
Patent; JNC Corporation; Tokyo Institute of Technology; Inouye, Satoshi; Sahara, Yuiko; Iimori, Rie; Hosoya, Takamitsu; US8546568; (2013); B2;,
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685-88-1, name is Diethyl fluoromalonate, belongs to esters-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. HPLC of Formula: C7H11FO4

Intermediate (5’B) (224.6 g, 698 mmols, 1.0 equiv.), methanol (2250 mL) and diethyl fluoromalonate (187 g, 1050 mmols, 1.5 equiv.) were charged to a suitable reaction vessel equipped with a mechanical stirrer and a digital thermometer. Then sodium methoxide in methanol solution (567 g, 30 wt. %, 3149 mmols, 4.5 equiv.) was charged via an addition funnel while maintaining the reaction temperature 20 to 35 C. The mixture was stirred at 20 to 35 C over 30 min. and a light suspension was obtained. The reaction was complete by HPLC. A solution of 1.5 N HC1 (2300 mL, 3450 mmols, 4.9 equiv.) was charged via an addition funnel over 1 h while maintaining the reaction temperature 20 to 30 C. A white suspension was obtained. The pH of the reaction mixture was to be ~1 by pH paper. The slurry was stirred at 20 to 30 C over 30 min. The resulting slurry was filtered, and the filter cake was washed with a pre-mixed solution of methanol and water (500 mL/500 mL), and then with water (1000 mL). The filter cake was dried under vacuum at 50 to 60 C over 16 h to furnish intermediate (6′) as an off-white solid (264 g, 97% yield, >99% pure by HPLC). – MR (500 MHz, DMSO-d6) delta ppm 12.82 (br. s., 1 H); 12.31 (br. s., 1 H); 9.14 (d, J=1.53 Hz, 1 H); 7.55 (s, 1 H); 7.31 – 7.37 (m, 1 H); 7.18 – 7.25 (m, 1 H); 7.10 – 7.15 (m, 2 H); 6.97 – 7.02 (t, J=7.55 Hz, 1 H); 5.88 (s, 2 H).

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; DUNBAR, Craig Anthony; SETHURAMAN, Vasu; HASHASH, Ahmad; (115 pag.)WO2017/95697; (2017); A1;,
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Electric Literature of 721-63-1, 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 721-63-1 as follows.

General procedure: Arylacetate(0.05mol) was dissolved in dry THF or toluene, and stirred in the ice bath.Sodium (0.075mol) was added to the solution, the mixture was stirred for 30 minin the ice bath. Ethyl formate (0.1mol) was added by dropwise to the above solution,the temperature of the reaction mixture was maintained at < 5 C.After the addition, the reaction mixture was stirred for another 2 h, thenwarmed to room temperature and stirred overnight (about 15 h). Water (50mL) wasadded to the slurry mixture, and stirred for an additional 30 min, thenportioned between organic layer and water. Water layer was extracted withdichloromethane (2×50mL). These extracts were discarded. The aqueous phase wasacidified with acetic acid or 5% hydrochloric acid, and extracted withdichloromethane (3×50mL). This extract was washed with water and brine, driedover anhydrous sodium sulfate, and the solvent was removed by rotaryevaporation under reduced pressure to give thick yellow oil, which was purifiedby column chromatography with ethyl acetate in petroleum ether. According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular. Reference:
Article; Liu, Jinbing; Chen, Changhong; Wu, Fengyan; Tang, Junyuan; Bioorganic and Medicinal Chemistry Letters; vol. 26; 7; (2016); p. 1715 – 1719;,
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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. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3-(4-fluorophenyl)propiolate

To a stirred solution of 1-aminopyridin-l-ium 2,4-dinitrophenolate (3.7 g, 13.30 mmol) and Intermediate 59A (2.4 g, 13.47 mmol) in THF (25 mL) was added DBU (4.06 mL, 26.9 mmol) dropwise at 0 C over a period of 10 min. and the resulting brown color solution was stirred at RT for 12 h. THF was removed completely under reduced pressure, crude product was diluted with water (100 mL) and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined the organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography (40 g REDISEP column, eluting with 2% methanol in chloroform). Collected fractions were concentrated together to afford Intermediate 59B (2.7 g, 74%) as a yellow solid. MS(ES): m/z = 271 [M+H]; 1H NMR (400 MHz, chloroform-d) delta ppm 8.52 (dd, J= 6.90, 1.07 Hz, 1H), 8.20 (dd, J= 8.94, 1.04 Hz, 1H), 7.76 – 7.85 (m, 2H), 7.43 (ddd, J= 8.97, 6.90, 1.07 Hz, 1H), 7.09 – 7.21 (m, 2H), 6.98 (td, J= 6.89, 1.22 Hz, 1H), 3.82 – 3.89 (m, 3H)

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 42122-44-1.

Reference:
Patent; KARUPPIAH Arul Mozhi Selvan Subbiah; KUMARAVEL Selvakumar; MAHESHWARAPPA Shilpa Holehatti; RACHAMREDDY Chandrasekhar Reddy; VELAPARTHI Upender; WITTMAN Mark D; WO2015/195880; (2015); 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. 5335-05-7, name is Chloromethyl benzoate, A new synthetic method of this compound is introduced below., Product Details of 5335-05-7

Preparation of iodomethyl benzoate (6) Compound 6 was prepared by a modification of a literature procedure (Maury et al , Org. Lett. 2010, 12, 3590). Chloromethyl benzoate (2.7 g, 15.9 mmol) was dissolved in acetone (20 mL). Sodium iodide (7.1 g, 47.6 mmol) was added, and the resulting mixture was stirred for 3 hours at 45 C, diluted with acetone (100 mL), filtered in the absence of light, and evaporated under reduced pressure at < 30 C. The residue was dissolved in diethyl ether (100 mL), washed with aqueous sodium bicarbonate and aqueous sodium thiosulfate, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure at < 30 C in the absence of light, yielding compound 6 as a yellow oil (3.3 g, 79%). The analytical data for compound 6 were identical to those reported in Maury el al , Org. Lett. 2010, 12, 3590. Compound 6 was used immediately in the subsequent step. 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; KALA PHARMACEUTICALS, INC.; ONG, Winston Zapanta; NOWAK, Pawel Wojciech; KIM, Jinsoo; ENLOW, Elizabeth M.; BOURASSA, James; CU, Yen; POPOV, Alexey; CHEN, Hongming; WO2014/144285; (2014); A1;,
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