Tag: M.W=100-200

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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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 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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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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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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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. 884497-46-5, name is Methyl 3-amino-5-fluorobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-amino-5-fluorobenzoate

To a solution of methyl 3-amino-S – fluorobenzoate (440mg, 2.6 mmol) in dry DMF (10 mL) was added Nail (187 mg, 7.8 mmol) portionwise, followed by addition of benzyl bromide (1.1 g, 6.5 mmol). The reaction mixture was stirred at 40 C for 1 6hr and concentrated. The resulting residue was purified by column chromatography to give the desired product. MS: 350 (M+1)

The synthetic route of 884497-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10626; (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. 13380-85-3, name is Methyl 4-(hydroxymethyl)cyclohexanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C9H16O3

In a nitrogen atmosphere, 10.0 g of the compound represented by Formula (I-105-1), 6.0 g of triethylamine, and 40 mL of tetrahydrofuran were added to a reaction container. While the resulting mixture was cooled with ice, 6.4 g of ethyl chloroformate was added dropwise to the mixture. The mixture was then stirred at room temperature for one hour. The precipitate was filtered away. In a nitrogen atmosphere, 2.2 g of sodium borohydride and 10 mL of tetrahydrofuran were added to another reaction container. While the resulting mixture was cooled with ice, the filtrate prepared above was added dropwise to the mixture. A liquid mixture of 40 mL of methanol and 10 mL of water was added dropwise to the mixture. The mixture was subsequently stirred at room temperature for three hours. After 20 mL of 10%-hydrochloric acid had been added to the mixture, extraction was performed with ethyl acetate. Then, purification was performed by column chromatography (silica gel, hexane/ethyl acetate). Hereby, 7.4 g of the compound represented by Formula (I-105-2) was prepared. (0129) In a nitrogen atmosphere, 7.4 g of the compound represented by Formula (I-105-2), 4.1 g of pyridine, and 35 mL of dichloromethane were added to a reaction container. While the resulting mixture was cooled with ice, 5.4 g of methanesulfonyl chloride was added dropwise to the mixture. The mixture was subsequently stirred at room temperature for three hours. The mixture was poured into water and then washed with 5%-hydrochloric acid and subsequently with a saline solution. Then, purification was performed by column chromatography (silica gel, hexane/ethyl acetate) and recrystallization (acetone/hexane). Hereby, 7.5 g of the compound represented by Formula (I-105-3) was prepared. (0130) In a nitrogen atmosphere, 25.0 g of the compound represented by Formula (I-105-4), 100 mL of acetic acid, and 100 mL of 48%-hydrobromic acid were added to a reaction container. The resulting mixture was heated to reflux for 12 hours. After the mixture had been cooled, it was poured into 1 L of water. Subsequently, extraction was performed with ethyl acetate, and washing was then performed with a saline solution. After the solvent had been distilled away, the remaining acetic acid was removed as an azeotrope with toluene. Then, purification was performed by column chromatography (alumina, ethyl acetate). Hereby, 12.0 g of the compound represented by Formula (I-105-5) was prepared. (0131) In a nitrogen atmosphere, 2.1 g of the compound represented by Formula (I-105-5), 7.5 g of the compound represented by Formula (I-105-3), 6.2 g of potassium carbonate, and 70 mL of N,N-dimethylformamide were added to a reaction container. The resulting mixture was stirred for 3 days while being heated at 90 C. The mixture was then poured into water. Subsequently, extraction with toluene and washing with a saline solution were performed. Then, purification was performed by column chromatography (silica gel, toluene) and recrystallization (toluene/hexane). Hereby, 4.8 g of the compound represented by Formula (I-105-6) was prepared. (0132) In a nitrogen atmosphere, 4.8 g of the compound represented by Formula (I-105-6), 20 mL of tetrahydrofuran, 20 mL of methanol, and 10 mL of a 25%-aqueous sodium hydroxide solution were added to a reaction container. The resulting mixture was stirred for 2 hours while being heated at 60 C. After the solvent had been distilled away, the residue was again dissolved in a mixed solvent of tetrahydrofuran and water. To the resulting solution, 10%-hydrochloric acid was added such that the pH of the solution became 2. After the solvent had been distilled away, water was added to the residue to precipitate a solid, which was filtered. The solid was washed with water and then dried. Hereby, 4.0 g of the compound represented by Formula (I-105-7) was prepared. (0133) To a reaction container, 15.0 g of the compound represented by Formula (I-105-8), 17.7 g of the compound represented by Formula (I-105-9), 16.0 g of potassium carbonate, and 100 mL of N,N-dimethylformamide were added. The resulting mixture was stirred for 12 hours while being heated at 80 C. After the mixture had been cooled and then diluted with dichloromethane, washing was performed with water and subsequently with a saline solution. Then, purification was performed by column chromatography (alumina, dichloromethane). Hereby, 24.2 g of the compound represented by Formula (I-105-10) was prepared. (0134) To a reaction container, 24.2 g of the compound represented by Formula (I-105-10), 60 mL of tetrahydrofuran, 60 mL of methanol, and 1 mL of concentrated hydrochloric acid were added. The resulting mixture was stirred at room temperature for eight hours. After the solvent had been distilled away, the residue was diluted with ethyl acetate. Subsequently, washing was performed with water and then with a saline solution. Then, purification was performed by column chromatography (alumina, ethyl acetate) and recr…

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; DIC Corporation; Kadomoto, Yutaka; Horiguchi, Masahiro; Koiso, Akihiro; (109 pag.)US2018/2276; (2018); 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. 584-74-7, name is Ethyl 2-fluorophenylacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Ethyl (2-fluorophenyl)acetate (900 mg, 5 mmol) and 60 % NaH (240 mg, 6 mmol) were dissolved in DMF (25 mL) and cooled to 0C. Cyclopentyl bromide (745 mg, 5 mmol) was added and the reaction was gradually warmed to rt. Reaction was stirred at rt for 16 h and then partitioned between EtOAc (100 mL) and NaHC03 (150 mL). The reaction was washed with brine (150 mL), dried over MgS04 and solvent was removed under reduced pressure. Saponification was conducted by addition of 2 M NaOH (20 mL) and heating at 60C for 16 h. The mixture was then acidified with 2 M aq HC1 and then extracted with EtOAc. The solution was dried over MgS04 and concentrated to give the title compound (yellow solid, 800 mg, 72 %). ? NMR (400 MHz, CDCl3) delta ppm 7.46 (t, .7=6.6 Hz, 1 H), 7.20 – 7.26 (m, 1 H), 7.12 (t, .7=7.5 Hz, 1 H), 7.05 (t, .7=9.2 Hz, 1 H), 3.78 (d, .7=11.0 Hz, 1 H), 2.47 – 2.60 (m, 1 H), 1.93-2.04 (m, 1 H), 1.54-1.75 (m, 3 H), 1.41-1.54 (m, 2 H), 1.29-1.41 (m, 1 H), 0.98-1.12 (m, 1 H).

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; UNIVERSITY HEALTH NETWORK; PAULS, Heinz W.; LAUFER, Radoslaw; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; LANG, Yunhui; PATEL, Narendra Kumar B.; EDWARDS, Louise G.; NG, Grace; SAMPSON, Peter Brent; FEHER, Miklos; AWREY, Donald E.; WO2013/53051; (2013); A1;,
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Electric Literature of 587-47-3,Some common heterocyclic compound, 587-47-3, name is Ethyl 2-(3-fluorophenyl)acetate, molecular formula is C10H11FO2, 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 ethyl 2-(3-fluorophenyl)acetate (18) (10.1 g, 55.0 mmol) inCCl4 (250 mL), is added with NBS (9.70 g, 55.0 mmol) and the mixture refluxed for 2 h at 800C (LC-MS monitoring: complete conversion). The solvent is evaporated and the resulting crude is dissolved in DCM and purified by filtration on a silica bed to obtain 7.80 g of (19) as a colorless oil (54% yield).

The synthetic route of 587-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; CALIGIURI, Antonio; RICCABONI, Mauro; AMARI, Gabriele; WO2010/72338; (2010); A1;,
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Related Products of 50893-36-2, 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. 50893-36-2, name is 1-Chloroethyl ethyl carbonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

50To a solution of 2-(3-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2- methyl-propionic acid [100 mg, 0.218 mmoL Example 49(b)] in dimethylformamide (2 mL) is added 1-chloroethyl ethyl carbonate (0.053 mL, 0.392 mmol) and Cs2CO3 (142 mg, 0.436 mmol). The mixture is heated under microwave at HO0C for 10 minutes, quenched with water, and extracted with ethyl acetate. Combined organic layers are washed with brine, dried over sodium sulfate and concentrated. The residue is subjected to silica gel chromatography eluting with 0 to 40percent EtOAc in heptane to obtain 2-(3-{6-[2-r2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenyl)-2- methyl-propionic acid 1-ethoxycarbonyloxy-ethyl ester as an oil

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

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/44732; (2006); A2;,
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