Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, belongs to esters-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 126541-82-0, Formula: C9H8F3NO2

Step A: Methyl 3-bromo-4-(trifluoromethyl)benzoatet-BuONO (79.0 g, 765 mmol) was added to a solution of methyl 3-amino-4- (trifluoromethyl)benzoate (67.0 g, 306 mmol) and CuBr (88.0 g, 612 mmol) in acetonitrile (1000 mL) at 0 C, and the resulting mixture was warmed to 25 C and stirred for 12 h. The mixture was then poured into EtOAc (600 mL) and filtered. The filtrate was washed with an aqueous HCl solution (1 M, 200 mL x 3), then brine (200 mL), dried over Na2S04 and concentrated. The residue was purified by column chromatography on silica gel (PE:EA = 200: 1) to give the title compound. MS: mlz = 283, 285 (M + 1). *H NMR (400 MHz, CDC13) delta 8.37 (s, 1H), 8.06 (d, J = 8.0 Hz, 1H), 7.77 (d, J= 8.0 Hz, 1H), 3.97 (s, 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 3-amino-4-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
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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 1559-02-0 as follows. SDS of cas: 1559-02-0

Synthesis of 1-Hydroxymethyl-cyclopropanecarboxylic acid ethyl ester A solution of lithium aluminum-tri-tert-butoxyhydride 1.0M in THF (28.5 mL, 28.5 mmol) is added to a solution of diethyl 1,1-cyclopropanedicarboxylate (2.0 mL, 11.4 mmol) in anhydrous THF (85.0 mL). After stirring the reaction mixture for 4 h, 10 mL of lithium aluminum-tri-tert-butoxyhydride 1.0M solution in THF is added and the solution is stirred for 18 h. The reaction mixture is diluted with DCM, washed with 1N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine. After drying the organic phase over anhydrous Na2SO4, removal of the solvent under reduced pressure affords 1.60 g of 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester that is used in the next step without further purification. Yield: 85%. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.88 (2H, q, J=4.1 Hz), 1.21-1.33 (5H, m), 2.59 (1H, t, J=6.9 Hz), 3.63 (2H, d, J=7.2 Hz), 4.17 (2H, q, J=7.1 Hz).

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); A1;,
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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. 6279-86-3, name is Triethyl methanetricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Triethyl methanetricarboxylate

Preparation of ethyl 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate In a round-bottomed flask equipped with a condenser, N-hexylaniline (355 mg, 2 mmol) is added to a solution of methanetricarboxylic acid triethyl ester (1.35 ml, 6.4 mmol). The resulting reaction mixture is placed in a CEM Discovery microwave oven and irradiated in the open round-bottomed flask, and then the ethanol formed is distilled off (the parameters are the following: power=250 W, temperature=225 C., execution time=5 min, hold time=15 min). After microwave heating, the reaction crude is purified on a chromatographic column, with petroleum ether, ethyl acetate at 4:1. The crystalline product obtained is dried to give the compound: yield=430 mg (69%). 1H NMR (CDCl3): delta 8.16 (d, J=8 Hz, 1H), 7.64 (m, 1H), 7.27-7.19 (m, 2H), 4.48 (q, J=8 Hz, 2H), 4.18 (t, J=8 Hz, 2H), 1.72-0.86 (m, 14H).

The synthetic route of 6279-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Ruat, Martial; Faure, Helene; Gorojankina, Tatiana; Mann, Andre; Taddei, Maurizio; Manetti, Fabrizio; Solinas, Antonio; US2013/267559; (2013); A1;,
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Application of 20372-66-1, 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 20372-66-1 as follows.

To a solution of 3-methoxyphenol (1 16 mg, 0.79 mmol) in DMSO (3 mL) was added potassium carbonate (218 mg, 1 .6 mmol) followed by methyl 2,4,5-trifluorobenzoate (150 mg, 0.79 mmol) . The resulting mixture was heated to 50C with stirring for 18 hours. The mixture was then cooled and diluted with water (30 mL) then washed with EtOAc (3 x 30 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford the title compound (154 mg, 66%) as an orange gum. 1H NMR (400 MHz, CDCI3): delta ppm 3.81 (s, 3H), 3.92 (s, 3H), 6.61 -6.69 (m, 3H), 6.76- 6.81 (m, 1 H), 7.31 (t, 1 H), 7.76 (dd, 1 H). LCMS Rt = 1 .76 minutes MS m/z 295 [MH]+

According to the analysis of related databases, 20372-66-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan Daniel; GALAN, Sebastien Rene Gabriel; MILLAN, David Simon; RAWSON, David James; STORER, Robert Ian; STUPPLE, Paul Anthony; SWAIN, Nigel Alan; WO2013/102826; (2013); A1;,
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Electric Literature of 34837-84-8, A common heterocyclic compound, 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate, molecular formula is C9H9FO2, 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.

Example 5; To a dry MEOH solution (50 ML) containing 4-FLUOROPHENYLACETIC acid 5A (5 g, 0.0324 mole) was added a catalytic amount of 4-toluene sulfonicacid (0.324 mmole, 61 mg). The solution was refluxed for 4 h. The resultant solution was concentrated under reduced pressure to give pale-yellow syrup. The material was diluted with EtOAc (100 mL), and neutralized with NAHCO3 (1M, 5 mL). The organic layer was then washed with H20 (10 mLx2), followed by brine (10 mL), dried over MGS04 and filtered. The filtrate was concentrated to give a pale-yellow liquid. (5.33 g, 31.75 mmole, 98 percent, MS M+H = 169 found: 169, 1H NMR structure confirmed). The methyl ester (2. 0g, 11.9 mmole) was then added to a CCL4 solution (100 mL) containing NBS (2.33 g, 13.09 mmole). The reaction mixture was refluxed at 80 °C for 3 h to yield the brominated methyl ester 5b. The cooled solution was filtered through a pad of silica gel to remove excess SUCCINIMIDE, the filtrate was evaporated under reduced pressure, and the resultant material was transferred to the next reaction without further purification. To an acetonitrile solution containing the amine (TBIA, 2.44 g (8.94 mmole) /15 mL ACN) was added the compound 5B (ca. 2 g). While the reaction mixture was stirred triethylamine was added dropwise (1.70 ML, 12.2 mmole 1.5 equiv. ). The reaction mixture was stirred at ambient temperature for 16 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and diluted with EtOAc (25 mL). The organic layer was treated with H2O, dried over MGS04, and filtered. The filtrate was then concentrated under reduced pressure to give the compound 5c, 3.29 g. Isobutyryl chloride (0.53 ML, 4.99 mmole in 5 mL DCM) was added dropwise to a chilled DCM solution (10 mL) containing the compound 5C (2.0 g, 4.54 mmole). While the reaction mixture was stirred, a triethylamine solution (1.27 ML, 2 equiv. in 5 mL DCM) was added dropwise. The reaction mixture was agitated as it was warmed to room temperature for 2 h. After completion of the reaction, the reaction mixture was treated with IN HCL (20 mL), followed by sat. NAHC03 (3 mL). The organic layer was then washed with water and brine, dried over MGS04, and filtered. The filtrate was concentrated under reduced pressure to give pale-yellow syrup. This was purified by a column chromatography using a gradient of EtOAc-Hexane mixture (from 0 to 25 percent of EtOAc). The isolated yield of the methyl ester was 2.10 g, 4.13 mmole, 90.9 percent. The methyl ester (250 mg, 0.50 mmole) was dissolved in a LIOH solution (1M, THF : water (5: 1) mixture), and vigorously stirred for 3 h. The reaction mixture was neutralized to pH 7 by titrating it with 1N HCL solution. The desired product was then extracted with EtOAc (20 mL). The organic layer was washed with H2O and brine, dried over MgS04, and filtered. The filtrate was then evaporated under reduced pressure to give a white amorphous material 5 (200 mg, 0.40 mmole, 80 percent, MS M+H = 496 found: 496, LU NMR structure confirmed).; Intermediate 2; Solution of 25.5 g (0.15 mol) of intermediate 1 in 50 ml of carbon tetrachloride was treated with 29.7 g (0.167 mol) of N-bromosuccinimide in 50 ml of carbon tetrachloride. Mixture was treated with 12 drops of HBR/HOAC (30percent) and stirred at reflux for 2h. Treated with another 5 g (0.03 mol) of N- bromosuccinimide and stirred at reflux for 2h. Cooled and reaction was filtered through a mixture of magnesium sulfate/silica gel (1: 1). Concentrated to yield 36.89 g of liquid.

The synthetic route of 34837-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/14539; (2005); A2;,
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Related Products of 150529-73-0,Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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.

Tributyltin methoxide (28.3 mL, 98 mmol), the product of preparation 8 (15.0 g, 65mol), isopropenyl acetate (10.8 mL, 98 mmol), palladium (II) acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100C for 5 hours. After cooling, the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90mL), and stirred for 15 minutes. The mixture was filtered through Arbocele and the organic phase was separated and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with diethyl ether : pentane, 0: 100 to 25: 75, followed by dichloromethane to give the title compound as a pale yellow oil in 94% yield (12.6 g). 1H NMR (400MHz, CDCI3) : 6 : 2.15 (3H, s), 3.61 (2H, s), 3.69 (5H, s), 7.10-7. 13 (2H, m), 7.19 (1H, d), 7. 30 (1H, t). LRMS ESI : m/z 229 [M+Na] +.

The synthetic route of 150529-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC; WO2005/92860; (2005); A1;,
Ester – Wikipedia,
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Application of 61367-07-5,Some common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, molecular formula is C8H16ClNO2, 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.

(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (4.08 g) obtained in Reference Example 2(1) is suspended in chloroform (50 ml), and thereto is added triethylamine (8.8 ml) under ice-cooling. Subsequently, a solution of 3-chloropropanesulfonyl chloride (3.35 ml) in chloroform (20 ml) is added dropwise over 20 minutes under the same temperature. After stirring for 2 hours at room temperature, 5 % hydrochloric acid is added to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diisopropylamine, and filtered to collect precipitates to give methyl trans-4-{[(3-chloropropyl)sulfonyl]amino}cyclohexanecarboxylate (6.14 g). APCI-MS M/Z:315/317[M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, its application will become more common.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Ester – Wikipedia,
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Reference of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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: In a glove box, add a ruthenium complex Il (0.75 mg, 0.001 mmol),Potassium methoxide (3.5 to 70 mg, 0.05 to 1 mmol), tetrahydrofuran (1 to 10 mL), and ester compounds (0.5 to 10 mmol).After sealing the autoclave, remove it from the glove box and fill it with hydrogen to the required pressure.The reaction vessel was stirred at room temperature for 16 to 24 hours.After slowly releasing excess hydrogen, the reaction solution was depressurized to remove the solvent, and the residue was purified by a short column of silica gel to obtain an alcohol compound.The results are shown in Table 7.

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
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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 6933-47-7 as follows. HPLC of Formula: C9H11NO2

Intermediate 7.5.24-tert-Butoxycarbonylamino-2-methyl-benzoic acid methyl esterTo a stirred solution of intermediate 7.5.1 (1.5 g) in dioxane (15 ml) at 10 C. was added a solution of Boc anhydride (2.2 g) in dioxane (15 ml) dropwise and the reaction allowed to warm to rt. After 3 h, dimethylaminopyridine (catalytic amount) was added. After overnight stirring, the mixture was concentrated, and the residue was purified by flash chromatography (dichloromethan with ethanol gradient 0 to 4%) affording 0.69 g of the title compound.ESI mass spectrum: [M+H]+=266

According to the analysis of related databases, 6933-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/28938; (2012); A1;,
Ester – Wikipedia,
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Synthetic Route of 6065-82-3, 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. 6065-82-3, name is Ethyl diethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of Ethyl diethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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