Month: March 2021

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 2150-38-1 as follows. Product Details of 2150-38-1

(1) Preparation of 3,4-dimethoxybenzoylacetonitrile Dry acetonitrile (1.8 ml) was added to a solution of n-butyl lithium (a 2.5M solution in hexane, 13.8 ml) in dry THF (30 ml) at -78 C., and the mixture was stirred at the same temperature for 1 hour. To the mixture was added a solution of methyl 3,4-dimethoxybenzoate (6.42 g) in dry THF (15 ml), and the mixture was stirred at -78 C. for 3 hours and then at room temperature for 1 hour. After adding water (100 ml), the reaction solution was extracted with ethyl ether (100 ml). After the aqueous layer was acidified with 6 N hydrochloric acid, it was extracted with ethyl acetate (200 ml*3). The organic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. Then the solvent was distilled away under a reduced pressure. The resulting residue was crystallized from ethyl acetate/hexane to obtain the title compound (3.6 g) as pale yellow crystals. 1 H-NMR (CDCl3) delta: 3.95 (3H, s), 3.97 (3H, s), 4.03 (2H, s), 6.92 (1H, d, J=9.0 Hz), 7.49 (1H, d, J=9.0 Hz), 7.51 (1H, s)

According to the analysis of related databases, 2150-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; US6043246; (2000); 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 3650-78-0 as follows. category: esters-buliding-blocks

To a stirred solution of benzyl bromide (27 mL, 227 mmol) in acetone at r.t. was added tetrahydrothiophene (10.0 mL, 1 14 mmol). The solution was stirred for 16 h and the resulting precipitate filtered and washed with acetone (3 x 50 mL) and dried under air, to give 1 -benzyltetrahydrothiophenium bromide as a white solid (51 .9 g, 88%). [00164] A mixture of 1 -benzyltetrahydrothiophenium bromide (3.39 g, 13.1 mmol) and (?)-methyl 3-(4-bromophenyl)acrylate (2.10 g, 8.71 mmol) in DCM (50 mL) was cooled to -78C and slowly treated with LiHMDS (13.1 mL, 1 M solution in THF) (via syringe pump, 1 mL/h). After complete addition, the mixture was warmed to r.t., stirred for 16 h and was quenched with H20 (50 mL). The biphasic mixture was separated and the organic layer washed with brine (2 x 50 mL), dried (MgS04) and concentrated. Purification by flash silica column chromatography (gradient elution i-hex to 5% EtOAc in i-hex) gave the title compound as a colourless oil (600 mg, 20%). LCMS (ES+) 332, 334 (M+H)+.

According to the analysis of related databases, 3650-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; LUCKHURST, Christopher, A.; BURLI, Roland, W.; STOTT, Andrew, J.; BRECCIA, Perta; WO2014/14900; (2014); A1;,
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Related Products of 40876-98-0, 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 40876-98-0 as follows.

Sten 1: Synthesis of ethyl 1 -(2-fluorobenzyl)-5 -hydroxy- 1 H-pyrazole-3 -carboxylate.A mixture containing acetic acid (15 equiv.) and diethyl oxalacetate sodium salt (1 equiv.) in benzene was stirred at 25 C for 30 mm. To this mixture was added (2-fluorobenzyl)hydrazine hydrochloride (2 equiv.). The resulting mixture was heated to 100 C for 2 h. The mixture was cooled to 23 C and concentrated under vacuum. The precipitate formed was collected by filtration. The solid was dissolved in ethyl acetate and washed with iN HC1 solution (x3). The organic layer was dried, filtered, and evaporated to give a solid containing the desired product. The solid was rinsed with a minimal amount of a methanol-diethyl ether mixture, dried under vacuum to deliver the desired intermediate, ethyl 1 -(2-fluorobenzyl)-5 -hydroxy-1H-pyrazole-3-carboxylate (11.8 g, 71 % yield) as a cream colored solid.?H NMR (500 MHz, CD3OD) ppm 7.24 – 7.41 (m, 1 H), 7.09 – 7.16 (m, 2 H), 7.02 – 7.07 (m, 1 H), 5.95 (s, 1 H), 5.29 (s, 2 H), 4.33 (q, 2 H), 1.36 (t, 3 H).

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; RENHOWE, Paul Allen; SHEPPECK, James Edward; NAKAI, Takashi; IYER, Karthik; PERL, Nicholas Robert; RENNIE, Glen Robert; WO2015/89182; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5335-05-7, name is Chloromethyl 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 5335-05-7, Recommanded Product: Chloromethyl benzoate

A solution of [2- (8, 9-DIOXO-2, 6-DIAZABICYCLO [5.2. 0] non-1 (7)-en-2-yl) ethyl]- phosphonic acid (20.16 MMOL, 5.25 g) in dry DMF (120 mL) was treated with N, N- diisopropylethylamine (80.64 MMOL, 14 ml) for’/2 hour at ambient temperature. Benzoic acid chloromethyl ester (60.49 MMOL, 10.32 g, synthesis described below) was added at ambient temperature under exclusion of moisture. The reaction mixture was heated to 65C for 20 hours. The temperature was then raised to 72C and stirred at 72C for 16 hours after which the reaction was completed. The mixture was cooled to room temperature and partitioned between 10% sodium bicarbonate and ethyl acetate. After separation of the layers the aqueous phase was again extracted with ethyl acetate (6x) until there was no more product in the water phase (by silica gel TLC, 7% 2M ammonia in methanol and 93% chloroform). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was flash chromatographed on 400 g silica gel using a solvent mixture of 1 % 2M ammonia in methanol and 99% chloroform. Gradually the percentage of ammonia in methanol was increased to 7% and 93% chloroform. The solvent was evaporated in vacuo to yield the desired product (10.5 g, 99%; glass like material). MS (ES-): m/e 527 (M-H).

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

Reference:
Patent; WYETH; WO2004/92189; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1117-71-1, 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. 1117-71-1 name is Methyl 4-bromobut-2-enoate, 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.

A solution of methyl (E) -4-bromocrotonate (6 g, 33.5 mmol) in THF (60 mL) was cooled to 0 C, an aqueous solution (20 mL) of lithium hydroxide monohydrate (1.83 g, 43.6 mmol) was added dropwise under N2. After 15 min dripping, keep 0 C for 3 h. The cold water (150 mL) and petroleum ether (200 mL) were then added to the system and stirring was continued at 0 C for 10 min. The aqueous phase was separated, adjusted to pH 1 with concentrated hydrochloric acid at 0 C and extracted with dichloromethane (80 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give E-4-bromocrotonic acid III as a yellow solid (4.5 g, yield 82%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromobut-2-enoate, and friends who are interested can also refer to it.

Reference:
Patent; Chengdu Zhipulai Bio-pharmaceutical Technology Co., Ltd.; Wang Kangmin; Zhao Gang; Liu Jifeng; Pu Lin; Chen Wei; (37 pag.)CN106946896; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 51122-91-9, 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. 51122-91-9, name is Dimethyl Isopropylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step (b): After the step (a), the reaction system was cooled to 90C, and (1E)-1,3-dichloro-1-propene (192.3 g) in toluene (250 ml) was added. After 2 hours of heating with stirring, the system was cooled to 50C, and water was added to terminate the reaction. The aqueous layer was extracted with diisopropyl ether (IPE), and the extract was combined with the organic layer and washed with water and 5% aqueous NaCl, successively. The solvent was evaporated under reduced pressure to give dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropylmalonate (409.7 g). The product contained 87% (GC purity) of dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropylmalonate and at most 0.5% (measured by GC) of isopropyl bromide, but did not contain the Z-isomer. 1HNMR (400 MHz, CDCl3): 0.98 (d, 6H, J=6.76), 2.31 (m, 1H), 2.62 (dd, 2H, J=1.16, 7.64), 3.73 (s, 6H), 5.89 (dt, 1H, J=7.60, 13.19), 6.01 (dt, 1H, J=1.16, 13.19). 13CNMR (400 MHz, CDCl3): 18.33, 32.41, 35.14, 51.94, 62.06, 119.83, 128.87, 170.66.

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, Dimethyl Isopropylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASAHI GLASS COMPANY LTD.; EP1571138; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, 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 26759-46-6, Computed Properties of C10H13NO4

Example 1: (Production of 6,7-dimethoxyquinazolin-4-one); Using acetic acid and an inorganic base, ammonia, as a catalyst, 6,7-dimethoxyquinazolin-4-one was produced in the manner mentioned below. 0.84 g (4 mmol) of methyl 4,5-dimethoxyanthranilate, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.05 g (2.8 mmol) of ammonia from a pressure cylinder were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with methanol and then dried in vacuum at 70C for 2 hours to obtain 0.77 g of a crystal. The obtained crystal was analyzed for the purity by high-performance liquid chromatography, and its purity was 99.5 %; and 6,7-dimethoxyquinazolin-4-one was obtained at a yield of 93.0 %. The result is shown in Table 1. Examples 2 to 4, and Comparative Examples 1 and 2: (Production of 6,7-dimethoxyquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 1, for which, however, the catalyst was changed as in Table 2. In Example 4, ammonium acetate was used as the catalyst; and in Comparative Examples 1 and 2, formic acid or potassium carbonate, respectively, was used alone as the catalyst like in JP-A 2002-338550 (Patent Reference 4). From the results in Table 1, it is known that the reaction system with acetic acid and a base coexisting therein of the present invention gives 6,7-dimethoxyquinazolin-4-one at a higher yield than the conventional reaction system with formic acid or potassium carbonate alone therein.

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 2-amino-4,5-dimethoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP1997812; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 79538-28-6, name is Methyl 2,4,6-trifluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H5F3O2

a) 4-Dimethylamino-2.6-difluoro-benzoic acid methyl ester (6a) To a stirred solution of 4,28 g (22.5 mmol) 2.4,6-Trifluoro-benzoic acid methyl ester (Apollo) and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 5h at 55C in an autoclave and is reduced with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 6a is obtained in 74 % yield (3.59 g, 16.7 mmol). MS-ESI: 216 (M+ +1,69).

According to the analysis of related databases, 79538-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

tert-Butyldimethylsilyl chloride (26.3 g, hydroxycyclohexanecarboxylate (25.0 g, 171 59-80-7) and imidazole (24.7 g, 363174 mmol) was added to a solution of ethyl 4-145 mmol, mixture of cis-/trans-isomers, Gas Nommol) in N,N-dimethylformamide (36 ml) and the mixture was stirred over night at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressure to yield ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104% yield) which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m, 0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

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 4630-82-4, A common heterocyclic compound, 4630-82-4, name is Methyl cyclohexanecarboxylate, molecular formula is C8H14O2, 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.

Step 1 : 1 -Allyl-cyclohexanecarboxylic acid methyl esterTo a solution of diisopropylamine (10 mL, 72 mmol) in tetrahydrofuran (100 mL) pre-cooled to -69C was added a 2.5 M solution of n-butyllithium in hexanes (29 mL, 72 mmol) dropwise. Following addition, the reaction mixture was warmed to 0C for 30 min and then re-cooled to -70C. To this mixture was added a solution of methyl cyclohexane carboxylate (8.9 mL, 60 mmol) in tetrahydrofuran (30 mL) dropwise. After stirring for 30 min, a solution of allyl iodide (7.2 mL, 78 mmol) in HMPA (5 mL) was added dropwise. The cooling bath was removed to allow the mixture to warm to 20C. After 1 .5 h, the reaction mixture was poured into H2O (200 mL). The two layers were separated and the aqueous layer was extracted with Et2O (100 mL). The organic layers were combined and dried over K2CO3, filtered and concentrated to afford 1 1 g of the title compound as an oil.

The synthetic route of 4630-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; GAO, Zhongli; HALL, Daniel; STEFANY, David; WO2011/143163; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics