Month: June 2021

Related Products of 14062-25-0, 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 14A Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate 1.45 g (36.2 mmol) of sodium hydride in mineral oil (60% pure) were initially charged in 100 ml of DMF. A mixture of 4.0 g (16.5 mmol) of ethyl (4-bromophenyl)acetate and 6.5 g (34.6 mmol) of 1,2-dibromoethane was dissolved in 50 ml of THF and slowly added dropwise. The mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 mum, 250 mm*40 mm (30% methanol/70% water to 100% methanol) over a run time of 25 min]. After HPLC control, the product-containing fractions were combined and concentrated. This gave 1.15 g (26% of theory) of a liquid. GC-MS [Method 5]: Rt=5.45 min; MS(ESIpos): m/z=268/270 (M+) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.09 (t, 3H), 1.16-1.20 (m, 2H), 1.46-1.50 (m, 2H), 4.02 (q, 2H), 7.26-7.31 (m, 2H), 7.47-7.51 (m, 2H)

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, Ethyl 2-(4-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECKER-PELSTER, Eva Maria; BUCHGRABER, Philipp; BUCHMUeLLER, Anja; ENGEL, Karen; GNOTH, Mark Jean; HIMMEL, Herbert; KAST, Raimund; KELDENICH, Joerg; KLAR, Juergen; KNORR, Andreas; LANG, Dieter; LINDNER, Niels; SCHMECK, Carsten; SCHOHE-LOOP, Rudolf; TINEL, Hanna; TRUeBEL, Hubert; WUNDER, Frank; (97 pag.)US2016/318866; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 61367-07-5, 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. 61367-07-5 name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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.

Step 1: Methyl (1r,4r)-4-(ethylsulfonamido)cyclohexane-1-carboxylate (0635) (0636) A solution of methyl (1r,4r)-4-aminocyclohexane-1-carboxylate hydrochloride (120 g, 0.62 mol) and Et3N (346 mL, 2.48 mol) in anhydrous DCM (2.5 L) was stirred at RT for 30 min. Ethanesulfonyl chloride (80.6 g, 0.63 mol) was added dropwise over 30 min to the reaction mixture at 0-5 C. After addition, the mixture was stirred at 0 C for 3 h. The mixture was quenched with water (250 mL) at 0 C. After partition, the organic layer was washed with H2O (600 mL, 5 volumes) and 1 N HCl (2 × 600 mL, 2 × 5 volumes), H2O (600 mL, 5 volumes) and brine (600 mL, 5 volumes), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford crude methyl (1r,4r)-4-(ethylsulfonamido)cyclohexane-1-carboxylate (117.6 g, 76%) as a light yellow solid, which was used for the next step without further purification.1H NMR (CDCl3400 MHz): delta 4.36 (d, J = 8.0 Hz, 1 H), 3.67 (s, 3 H), 3.29-3.22 (m, 1 H), 3.04 (q, J = 7.6 Hz, 2 H), 2.25-2.21 (m, 1 H), 2.15-2.09 (m, 2 H), 2.08-2.01 (m, 2 H), 1.58-1.51 (m, 2 H), 1.39-1.25 (m, 5 H).

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

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 52787-14-1 as follows. COA of Formula: C11H12O4

To a mixture of K2CO3 (1194.5 g), homoterephthalic acid dimethyl ester (600 g) in DMAc (3000 mL), propargyl bromide (582.43 g) was added followed by TBAI (106.41 g) at 25-30 C. and stirred for 20-26 hours. The reaction was monitored by HPLC and found the ratio of Monopropargyl homoterephthalic Acid Dimethyl Ester to that of dipropargyl homoterephthalic Acid Dimethyl Ester to be not less than 85:15. After 26 hours the reaction mixture was quenched with DM water (3000 ml) and extracted with ethyl acetate (2*3000 ml). The organic layer was separated and back-extracted with DM water (3000 ml). The organic layer was then evaporated to dryness at reduced pressure on a rotary evaporator (below 60 C.). Further IPA (1000 ml) was added to the residue and evaporated to dryness at reduced pressure. The crude product was crystallized by dissolving in IPA (000 ml) at 45-50 C. and cooled to 0-5 C. and stirred for 1-2 hours. The product was vacuum filtered. The product obtained was further crystallized with IPA (1800 ml) saturated with Ethyl acetate (54 ml) by dissolving at 55-60 C. and stirred at 20-25 C. for 2-3 hours, followed by stirring at 0-5 C. for 2-3 hours. The solid was filtered and dried under vacuum at 40-45 C. to give 466 g (65.6%) of the title compound. Purity: 99.19%

According to the analysis of related databases, 52787-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fresenius Kabi Oncology Limited; Lahiri, Saswata; Gupta, Nitin; Singh, Hemant Kumar; Panda, Nilendu; Handa, Vishal; Abul, Azim; Gupta, Chandan Kumar; Sanghani, Sunil; Sonavane, Ghanashyam Madhukar; US2015/183789; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 59833-69-1, 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. 59833-69-1, name is Methyl 2-(3-amino-4-chlorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of 35c (781 mg, 3.9 mmol) and pyridine (0.95 mL, 11.7 mmol) in CH2Cl2 (10 mL) was added a solution of 34a (1.3 g, 3.9 mmol) in CH2Cl2 (10 mL). After stirring overnight at room temperature, the reaction mixture was quenched with water and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (1.3 g, 63% in 2 steps) as a pale yellow amorphous powder.

The synthetic route of Methyl 2-(3-amino-4-chlorophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iwahashi, Maki; Naganawa, Atsushi; Kinoshita, Atsushi; Shimabukuro, Atsushi; Nishiyama, Toshihiko; Ogawa, Seiji; Matsunaga, Yoko; Tsukamoto, Kohki; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Oumi, Rie; Odagaki, Yoshihiko; Katagi, Jun; Yano, Koji; Tani, Kousuke; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 22; (2011); p. 6935 – 6948;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 15012-36-9,Some common heterocyclic compound, 15012-36-9, name is Methyl 2,3-dimethylbenzoate, molecular formula is C10H12O2, 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 2,3-dimethylbenzoate (2.0 g, 12.2 mmol) in 1,2-dichloroethane (10 mL) were added chloromethyl methyl ether (5 mL, 36.0 mmol), thionylchloride (0.36 mL, 5.0 mmol) and ferric chloride (0.4 g, 2.4 mmol) at 0 C. The resulting mixture was heated to 55 C for 2 h. After cooling to room temperature, the mixture was extracted with EtOAc (3 x 100 mL) and washed with water (20 mL) and brine (20 mL). The combined organic extracts were dried over anhydrous Mg504, filtered and concentrated.Silica gel chromatography (hexane:EtOAc) afforded the title compound (1.1 g). MS (ES) m/z 213 (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 2,3-dimethylbenzoate, its application will become more common.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; HUDSON, Ryan; BEAUSOLEIL, Anne-Marie; (616 pag.)WO2018/89261; (2018); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1150566-27-0, 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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (500.0 mg, 2.21 mmol) in dioxane:EtOH:H2O (4:1:3, 9 mL), (3,5-dimethylisoxazol-4-yl)boronic acid (404 mg, 2.87 mmol), Cs2CO3 (1.45 g, 4.42 mmol) and Pd(PPh3)4 (127.0 mg, 0.11 mmol) were added and the reaction was refluxed for 15 h. After cooling to room temp, the solvents were evaporated and the solid was taken up in THF (6 mL). A solution of LiOH (106.0 mg, 4.42 mmol) in 0 (3 mL) was added, the mixture was stirred for 15 h. The solvent was removed under reduced pressure and the residue was acidified to pH 4 with 3N HCl. The volatiles were evaporated under reduced pressure and the solid was triturated with MuepsilonOmicronEta:0 (1:1). Upon filtration 6-(3,5-dimethylisoxazol-4-yl)imidazo[1,2-b]pyridazine-3-carboxylic acid was obtained (331.0 mg, 58%). MS (ESI) calcd for C12H10N4O3: 258.1; found: 258.9 [M+H]

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, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 18469-52-8, A common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, molecular formula is C9H11NO2, 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.

The compound 2,4-dichloro-6-nitro-quinazoline (0.115 g, 0.47 mmol) was weighed in a reaction flask,Isopropyl alcohol 4mL,Stir into suspension,Methyl p-aminomethylbenzoate (0.094 g, 0.56 mmol) and DIEA (0.106 g, 0.82 mmol) were added,Reaction at room temperature 2.5h.Stop stirring, add dichloromethane to make the reaction solution becomes clear, add silica gel,Concentration by column chromatography [petroleum ether / ethyl acetate = 10: 1 (v / v) / methylene chloride / ethyl acetate = 10: 1 (v / v)] gave 0.162 g of a yellow solid in a yield of 92.6%

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; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Jin Jing; Zhu Lina; Zhang Chongjing; (85 pag.)CN102250075; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 57625-74-8,Some common heterocyclic compound, 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, molecular formula is C11H14O2, 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 C. To a suspension ofAlCl3 (500.0 mg, 3.75 mmol) inCH2Cl2 at-10 C was added dropwise oxalyl chloride (476.0 mg, 3.75 mmol) inCH2C12. The mixture was stirred at this temperature for 30 min. Then a solution of 2-methyl-2- phenyl-propionic acid methyl ester (178.0 mg, 1.0 mmol) inCH2C12 was added. The resulted mixture was stirred at-10 C for 1 hr and rt overnight. The mixture was filtered through a pad of celite, the solvent and excess oxalyl chloride was removed under reduced pressure. The residue was dissolved in chlorobenzene and refluxed for 4 hr. Solvent was removed and the residue was dried to give2- (4- chlorocarbonyl-phenyl) -2-methyl-propionic acid methyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-methyl-2-phenylpropanoate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99276; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 42122-75-8, These common heterocyclic compound, 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, 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 1 2-Chloro-N-(1 -hydroxy-cyclohexylmethyl)-5-phenylamino-benzamide1.1 2-Chloro-5-Dhenylamino-benzoic acid methyl esterCs2C03 (2.79 g), palladium(ll) acetate (82 mg), 2,2′-bis(diphenylphosphino)-1 ,1 ‘- binaphthalene (228 mg), iodobenzene (0.69 mL) and methyl-5-amino-2-chlorobenzoate (1.13 g) were placed in a flask and flushed with argon. Dioxane (18 mL) was added and the reaction mixture was heated to 100C for 24h. After cooling to RT, it was diluted with Et20, filtered over a pad of celite and the filtrate was concentrated in vacuo. The crude material was purified by CC (Hept/EtOAc 1/0 to 8/2) to give 1.18 g of the titled compound as a light yellow solid.LC-MS (A): tR = 1 .05 min; [M+H]+: 262.55.

The synthetic route of 42122-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; WO2012/114268; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 443-26-5, name is Ethyl 2-fluorobenzoate, 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. COA of Formula: C9H9FO2

REFERENCE EXAMPLE 191 Methyl 4-(4-Methoxybenzenesulfonyl)-1-[2-(1-pyrazolyl)phenylcarbonyl]-7-methyl-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate As described for the general reaction of ethyl 2-fluorobenzoate with amines set forth in Tetrahedron, 53, 7557-7576 (1997), ethyl 2-fluorobenzoate was reacted with pyrazole by refluxing N, N-dimethylformamide to give ethyl 2-(1-pyrazolyl)benzoate, as a thick yellow oil. Anal. Calc’d: for C12H12 N2O2: C, 66.7,H, 5.6; N 13.0: Found: C, 66.5:H, 5.4: N, 12.9; Mass spectrum (ES) 217.2 (M+H).

The synthetic route of Ethyl 2-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6544984; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics