Month: July 2021

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. 29006-01-7, name is Methyl 4-methoxybutanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 4-methoxybutanoate

Description 374-Methoxybutanoic acid (P37)To a solution of methyl 4-methoxybutanoate (555.6 mg) in THF (6 mL), sodium hydroxide (6.31 mL) (2M aqueous solution) was added, the reaction mixture was stirred overnight. Most solvent was removed by rotavap, diluted with water (5 mL), washed with DCM (5 mL). The aqueous layer was acidified with 3 M HC1 (aq.) to pH 2, extracted with EtOAc twice (2x 15 mL). The combined organic layer was dried over Na2504 and filtered. The filtrate was concentrated to afford the titlecompound (491.3 mg) as colorless oil. 111 NMR (400 MHz, DMSO-d6): 12.02 (s, 1H), 3.30 (t, J=6.6 Hz, 2H), 3.21 (s, 3H), 2.23 (t, J= 7.3 Hz, 2H), 1.71 (quin, J= 6.9 Hz, 2H).

According to the analysis of related databases, 29006-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DENG, Jing; LEI, Hui; MA, Xin; LIN, Xichen; WO2015/180612; (2015); A1;,
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Reference of 18014-00-1, 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 18014-00-1 as follows.

General procedure: To a 15 mL vial tube equipped with a magnetic stirring bar and a teflon screw cap were addeddimethyl 2,5-dibromoterephthalate (0.28 g, 0.8 mmol),1) N-methylaniline derivative (8.0 mmol),Pd2(dba)3 (34 mg, 0.06 mmol), RuPhos (70 mg, 0.24 mmol), K3PO4 (1.70 g, 8.0 mmol), and toluene(3.2 mL) under argon atmosphere. The mixture was stirred at 100 C for 10 h. The resultingmixture was allowed to cool to room temperature, and CH2Cl2 (10 mL) was added to the vial. Theprecipitate was removed by suction filtration and the filtrate was concentrated by evaporation underreduced pressure. The crude product was purified by column chromatography on silica gel(hexane/CH2Cl2 2:1 to 1:1) to give 1.

According to the analysis of related databases, 18014-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shimizu, Masaki; Asai, Yuiga; Takeda, Youhei; Yamatani, Akinori; Hiyama, Tamejiro; Tetrahedron Letters; vol. 52; 32; (2011); p. 4084 – 4089;,
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Application of 555-43-1, A common heterocyclic compound, 555-43-1, name is Propane-1,2,3-triyl tristearate, molecular formula is C57H110O6, 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.

General procedure: Into a single-necked reaction flask, 1 equivalent of myristin (0.27 g, 0.37 mmol) and 3 equivalents of 11-(hexadecylthio)undecan-1-ol (0.48 g, 1.12 mmol) were added. After the addition of the catalyst (0.030 g, 15 mmol%), the mixture was heated with stirring in glycerin bath at 110 C (bath temperature) for 6 h, at the end of which the reaction mixture was cooled and sufficient amount of MeOH was added. The resulting solid product was filtered under vacuum and washed successfully with MeOH. The yield of 11-(hexadecylthio)undecyl tetradecanoate was 0.67 g, 93%. The productis of sufficient purity for further spectroscopic analysis.

The synthetic route of 555-43-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Y?ld?r?m, Ayhan; K?raylar, Kaan; Oeztuerk, Serkan; Research on Chemical Intermediates; vol. 46; 1; (2020); p. 215 – 230;,
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Application of 29006-01-7, The chemical industry reduces the impact on the environment during synthesis 29006-01-7, name is Methyl 4-methoxybutanoate, I believe this compound will play a more active role in future production and life.

Step 1. 4-Methoxybutanal [00207] To a solution of methyl 4-methoxybutanoate (3.43 g, 26 mmol) in DCM (26 mL) was added DIBAL-H (33 mL, 33 mmol, 1 M in toluene) at -78 C. After stirring at -78 C for 50 mins, the reaction was quenched with MeOH (10 mL) and then brine (20 mL). The separated organic layer was dried over Na2S04, concentrated in vacuo to give 4-methoxybutanal (2.25 g, 85%) as colorless liquid, which was used in the next reaction without further purification.

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-methoxybutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; KARRA, Srinivasa R.; GOUTOPOULOS, Andreas; (137 pag.)WO2016/19228; (2016); 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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 4-amino-3-fluorobenzoate

3.101. Compound 95: 4-{[4-(Cyclopropanecarbonyl-amino)-l-methyl-lH-imidazo[4,5- c]pyridin-6-yl]-methyl-amino}-3-difluoromethoxy-5-fluoro-benzamide 3.101.1. Step i): 4-Amino-3-fluoro-5-iodo-benzoic acid methyl ester Iodine (1 eq, 3.76 g) is dissolved in EtOH (80 mL) at room temperature followed by the addition of 4-amino-3-fluoro-benzoic acid methyl ester (1 eq, 2.5 g) and silver sulfate (1 eq, 4.61 g). After lh, the silver salts are filtered off and the filtrate is concentrated under reduced pressure. The residue is dissolved in DCM and washed with sat. Na2S203, passed through a phase separator and concentrated to afford the desired product that is used as such in the next step.

According to the analysis of related databases, 185629-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
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Related Products of 34837-84-8, 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. 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 20: 4-Fluorophenylacetic acid 1 (Z = COOCH3, F = 4-F, X = H)10 mL water and 0.8 mL of a 30percent sodium hydroxide solution is added to 0.3 g methyl 4-fluorophenylacetate and the mixture is stirred at 60° C for an hour. Once the conversion is completed, it is acidified with concentrated hydrochloric acid to pH = 1. The product is isolated by filtration as a white solid in a 0.15 g (55percent) amount.1H-NMR (300 MHz, CDCl3): delta (ppm) : 3.63 (s, 2H); 7.02 (t, 2H); 7.24 (t, 2H); 10.1 (bs, IH).

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-(4-fluorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.I.S. FABBRICA ITALIANA SINTETICI S.P.A.; WO2008/78350; (2008); A2;,
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Reference of 29547-04-4, A common heterocyclic compound, 29547-04-4, name is Methyl 2,4-dibromobutanoate, molecular formula is C5H8Br2O2, 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 N1,N2-dibenzylethane-1,2-diamine (11.20 g, 46.60 mmol) and TEA (13.00 mL, 93.20 mmol) in toluene (80 mL) was added the solution of methyl 2,4- dibromobutanoate (12.10 g, 46.60 mmol) in toluene (110 mL) dropwise at RT. The reaction mixture was stirred for 16 hours at 80C. The resulting mixture was poured into aqueous sat?d Na2CO3 solution (60 mL) and extracted with EA (3 x 50 mL). The combined organic layers were washed with brine (3 x 80 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under vacuum. The residue was purified by a silica gel column chromatography, elutingwith 20% EA in PE to afford the title compound: LCMS [M + 1]+: 339.

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; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; SCOTT, Jack, D.; TANG, Haiqun; ZHAO, Zhiqiang; YANG, Dexi; GU, Xin; JIANG, Jinlong; XIAO, Li; (209 pag.)WO2019/18186; (2019); A1;,
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Electric Literature of 175867-59-1,Some common heterocyclic compound, 175867-59-1, name is Methyl 4-aminocyclohexanecarboxylate, molecular formula is C8H15NO2, 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 methyl 4-aminocyclohexane-1-carboxylate (0.61 g from step a) in DCM (5 mL), at RT, a solution of Boc20 (0.14 g, 0.64 mmol) in DCM (0.5 mL) was added portion-wise and the resulting reaction mixture was stirred at RT. The reaction mixture was concentrated under vacuum and the crude product was purified by FC on silica cartridge (eluting with Cy/EA from 100/0 to 90/10) affording methyl 4-{[(tert- butoxy)carbonyl]amino}cyclohexane-1-carboxylate (p229, 0.24 g, y= 22%). MS (m/z): 258.3 [MH]+.

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

Reference:
Patent; INDIVIOR UK LIMITED; CREMONESI, Susanna; MICHELI, Fabrizio; SEMERARO, Teresa; TARSI, Luca; (364 pag.)WO2016/67043; (2016); A1;,
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Electric Literature of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, 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.

(2) Compound 2 (4.0 g), Compound 3(3.52 g),[1,1′-bis (diphenylphosphino) ferrocene] palladium (II)Dichloromethane adduct (1.43 g)And potassium carbonate (7.24 g)Of N, N-dimethylformamide (80 mL)Under a nitrogen atmosphere,And the mixture was stirred at 80 C. for 6 hours.To the reaction mixture was added diethyl ether (200 mL)And the mixture was stirred, and insoluble matter was removed by filtration.Water and ethyl acetate were added to the filtrate, followed by stirring,And extracted with ethyl acetate.The obtained organic layer was washed with water and saturated brine,Dried and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 to 80:20) to obtain Compound 4 (2.78 g) As a pale yellow viscous substance.

The synthetic route of 87808-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma; Sato, Atsushi; Imashiro, Ritsuo; Tuzisima Tosinori, Shuichi; Tanimoto, Koichi; Yamamoto, Yasuo Wang; Nakane, Tetsuya; Erikawa, Chihiro; (123 pag.)JP2018/199673; (2018); A;,
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Electric Literature of 40872-87-5, The chemical industry reduces the impact on the environment during synthesis 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, I believe this compound will play a more active role in future production and life.

Methyl 4-chloro-3-cyanobenzoate (2). To a solution of methyl 3-amino-4- chlorobenzoate (15.0 g, 81.0 mmol) in H20/conc. HC1 (150 mL/17 mL), nitrous acid solution (5.6 g, 81 mmol) was added drop-wise at 0C and stirred for 30 min. The reaction mixture was neutralized with sodium hydroxide solution. The resulting diazonium salt solution was added to a solution of cuprous chloride (8.0 g, 81.0 mmol) and sodium cyanide (10.7 g, 218.0 mmol) at 0 C and stirred at room temperature for 4h. The reaction mixture was quenched with water (150 mL) and extracted with ethyl acetate (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude obtained was triturated with diethyl ether and n-pentane to yield 2 (8.0 g, 51%) as a white solid. 1H NMR (400 MHz, CDCI3) delta 3.88 (s, 3H), 4.26 (brs, 2H), 7.29 (d, J = 8.2 Hz, 1H), 7.34-7.37 (dd, J =1.9, 8.2 Hz, 1H), 7.45 (d, J = 1.9 Hz, 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 3-amino-4-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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