Tag: M.W=200-300

Reference of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, 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 724: 2-(2-cyclopropylmethoxy-5-fluoro-4′-trifluoromethyl-biphenyl-4-yl)-4- methyl-pentanoic acid. Step lDiethyl 2-(2,5-difluoro-4-nitrophenyl)-2-isobutylmalonate2-Isobutylmalonic acid diethyl ester (40.Og, 0.185 mol) in DMF (5OmL) was added dropwise to a stirred suspension of sodium hydride (60% in mineral oil, 8.0g, 0.33 mol) in 200 mL DMF (20OmL) over 20 min. at O0C under nitrogen. The mixture was stirred for 0.5 h at room temperature, cooled to 0 C and l,2,4-trifluoro-5-nitro-benzene (30.0g, 169.5 mmol) in DMF (15OmL) was added dropwise. The resulting reaction mixture was stirred at room temperature for 16h, poured into ice water (20OmL) and extracted with EtOAc (3x10OmL). The combined organic phases were washed with water (3x10OmL), brine (10OmL) and dried (MgStheta4). Evaporation of solvent under reduced pressure gave a brown oil which was purified by column chromatography over silica gel (Heptane-EtOAc, gradient) to give 57.0 g (90%) of 2-(2,5- difluoro-4-nitrophenyl)-2-isobutylmalonic acid diethyl ester as yellow oil. H NMR (300 MHz, CDCVTMS): delta 7.87 (dd, J = 12.3, 6.0 Hz, IH), 7.79 (dd, J = 10.1, 6.4 Hz, IH), 4.30^1.18 (m, 4H), 2.27 (d, J = 5.8 Hz, 2H), 1.60-1.50 (m, IH), 1.26 (t, J = 7.1 Hz, 6H), 0.82 (d, J = 7.0 Hz, 6H); 13C NMR (75 MHz, CDCI3/TMS): delta 168.2, 155.1 (d, 1JcF = 252.3 Hz), 150.9 (d, 1JcF = 263.2 Hz), 135.7, 135.1, 120.0 (dd, 2JCF = 26.0, 3JCF = 4.0 Hz), 113.0 (d, 2JCF = 29.0 Hz), 62.3, 43.1, 24.9, 23.8, 13.8.

The synthetic route of 10203-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; WO2009/86277; (2009); A1;,
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Related Products of 1014645-87-4, 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. 1014645-87-4 name is Methyl 4-(1-aminocyclopropyl)benzoate 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.

To a solution of 2,5-dichloronicotinic acid (1.84 g, 7.06 mmol) in dry dimethylformamide (15 ml) 1-Hydroxybenzotriazole hydrate (1.08 g, 7.06 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03 g, 10.58 mmol), a solution of methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (1.67 g, 7.06 mmol) and triethylamine (0.98 ml, 7.06 mmol) in dry dimethylformamide (15 ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4Cl saturated solution (50 ml) was added the mixture was extracted with ethylacetate (3×50 ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50g) eluting with a mixture dichloromethane/ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1.03 mg)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, A new synthetic method of this compound is introduced below., COA of Formula: C14H17NO4

General procedure: Anilinomethylenemalonates 8a-c (3 g, 10.83 mmol) were refluxed for 30 min in diphenyl ether (30 mL), leading to crude oxoquinolines 9a-c which were recrystallized from dimethylformamide [20,21,26,27].

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Forezi, Luana Da S. M.; Tolentino, Nathalia M. C.; De Souza, Alessandra M. T.; Castro, Helena C.; Montenegro, Raquel C.; Dantas, Rafael F.; Oliveira, Maria E. I. M.; Silva Jr., Floriano P.; Barreto, Leilane H.; Burbano, Rommel M. R.; Abrahim-Vieira, Barbara; De Oliveira, Riethe; Ferreira, Vitor F.; Cunha, Anna C.; Boechat, Fernanda Da C. S.; De Souza, Maria Cecilia B. V.; Molecules; vol. 19; 5; (2014); p. 6651 – 6670;,
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Electric Literature 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 7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-10 tetrahydroquinoline (Intermediate C,700 mg,2. 67mmo ),ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (600 mg,2.67 mmol)and K3P04 (1.69 g,7.98 mmol)in 2-methyl-2-butanol (10 mL)was added methanesulfonato(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1’biphenyl)(2′-amino-1,1′-biphenyl-2-yl)palladium(II)(225 mg,0.27 mmol). The mixture washeated to 95 C for 12 h under an argon atmosphere. After cooling the reaction to room15 temperature,the mixture was filtered and concentrated in vacuo. The crude residue was purifiedby Prep-TLC (petroleum ether I EtOAc = 1 : 1)to give the title compound (110 mg,9%)asyellow oil. LCMS M/Z (M+H)453

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 756525-95-8, Formula: C11H23NO4

Acetylenedicarboxylic acid (26.5 mg, 0.232 mmol, 1.0 eq.) was dissolved in NMP (1.0 mL) and cooled to 0 C, to which compound 159 (0.15 g, 0.557 mmol, 2.4 eq.) was added, followed by DMTMM (0.18 g, 0.65 mmol, 2.8 eq.) in portions. The reaction was stirred at 0 C for 5 h and then diluted with ethyl acetate and washed with water and brine. The organic solution was concentrated and purified by column chromatography (80-90% EA/PE). The appropriate fractions were concentrated and kept in refrigerator overnight. A solid formed and was filtered off. The filtrate was concentrated to give a light yellow oil (0.37 g, >100% yield), which was used without further purification. MS ESI m/z calcd for C26H45N2O10 [M+H]+ 545.30; found 545.30.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 9-Amino-4,7-dioxanonanoate, and friends who are interested can also refer to it.

Reference:
Patent; SUZHOU M-CONJ BIOTECH CO., LTD.; HANGZHOU DAC BIOTECH CO, LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; GAI, Shun; ZHAO, Linyao; YE, Hangbo; GUO, Huihui; TONG, qianqian; CAO, Minjun; JIA, Junxiang; YANG, Chengyu; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; LIN, Chen; GUO, Zhixiang; YE, Zhicang; (246 pag.)WO2016/59622; (2016); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 59247-47-1, name is tert-Butyl 4-bromobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl 4-bromobenzoate

To a 100 mL round-bottom flask purged with and maintained under an inertatmosphere of nitrogen was added a solution of (1 S,4R,5R)-5-[[3-(2-chloro-6-t1uorophenyl)-5-cyclopropyl-L2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1 ]heptan-3-one 306h (220 mg,0.58 mmol, 1.00 equiv.) in 1,4-dioxane (8 mL), tert-butyl4-bromobenzoate (180 mg, 0.7030 nm10l, 1.20 equiv.), Xantphos (51 mg, 0.09 mmol, 0.15 equiv), Pd2(dba)1 (27 mg, 0.03 mmol,0.05 equiv.), and Cs2C01 (286 mg, 0.88 mmol, 1.50 equiv.). The resulting mixture washeated at l05°C overnight After cooling to room temperature, the mixture was diluted with 50 mL ofvvater, and extracted with 200 mL of ethyl acetate. The organic extract was washedwith brine (lOO mL), dried over anhydrous sodiurn sulfate and concentrated lmder vacuum.The residue vas purified by silica gel column chromatography eluting with ethylacetate/petroleum ether (1 :4) to afford tert-buty 14-[(1 S,4R,5R)-5-[ [3-(2-chloro-6-5 t1uorophenyl)-5-cyclopropyl-l ,2-oxazol-4-yl]meihoxy ]-3-oxo-2-azabicyclo[2. 2.1 ]heptan-2-yl]benzoate 306c (250 mg, 77percent) as a yellow oil

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; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6138-26-7,Some common heterocyclic compound, 6138-26-7, name is Trimethyl propane-1,2,3-tricarboxylate, molecular formula is C9H14O6, 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.

In a reactor equipped with a stirrer, a thermometer, a condensing tube, and a Dean-Stark trap, 4-hydroxy-2,2,6,6-tetramethylpiperidine (4.32 g), 1,2,3-propanetricarboxylic acid trimethyl ester (2.00 g), and dibutyl tin oxide (0.28 g) were dissolved in xylene (28 mL), and the resulting solution was refluxed under heating for 48 hours in a nitrogen atmosphere. During the course, generated methanol was removed by molecular sieves. The resulting product was cooled to room temperature and then washed by adding water. The resulting product was purified by recrystallization, and (I-1-a) was obtained as colorless powder. The yield was 1.12 g. The melting point was 110 C.1H-NMR (400 MHz, CDCl3): 1.05-1.16 (m, 24H), 1.21 (s, 18H), 1.87-1.92 (m, 6H), 2.54 (dd, J=6.2 Hz, 16.6 Hz, 2H), 2.70 (dd, J=7.1 Hz, 16.6 Hz, 2H), 3.16-3.23 (m, 1H), 5.13-5.23 (m, 3H).GC-MS (EI): m/z 594 [M+H+], 578 [M-15+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Trimethyl propane-1,2,3-tricarboxylate, its application will become more common.

Reference:
Patent; DIC CORPORATION; Iwakubo, Masayuki; Nose, Sayaka; Takachi, Manabu; Aoki, Yoshio; (13 pag.)US10336939; (2019); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, 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 88709-17-5, name: Ethyl 2-ethoxy-4-methylbenzoate

To the reaction kettle were added ethyl 4-methyl-2-ethoxybenzoate (2.08 g, 10 mmol), ethanol (23 g, 0.50 mol), tetrahydrofuran (100 mL), and tert-peroxybutyl ether (1.75 g, 10 mmol) in this order. , PdCl2 (54.3 mg, 0.3 mmol) and 1,2-bis (di-2-pyridylphosphine) ethane (123.3 mg, 0.3 mmol), charged with 2.0 MPa of CO, heated to reflux, and stirred for 20 hours. After cooling to room temperature, a 2 mol / L sodium hydroxide aqueous solution (30 mL) was added to the reaction solution after depressurization. After stirring for 6 hours, cyclohexane (50 mL × 3) was added to wash the reaction solution. The reaction solution was neutralized with hydrochloric acid to a pH of 7, The solution was concentrated under pressure to about 50 mL, hydrochloric acid was acidified to pH 3, a yellow solid was precipitated, and the residue was recrystallized from toluene-petroleum ether to obtain a white solid intermediate (I) (1.94 g, yield: 76.9%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yu Rui; Hong Xuming; Zheng Min; Shao Qingling; (8 pag.)CN110483292; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 59247-47-1,Some common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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 solution of tert-butyl 4-bromobenzoate (616 mg, 2.4 mmol) in 1,4-dioxane and water (4:1, 10 mL) were added (E)-4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane (553 mg, 2.4 mmol), tetrakis(triphenylphosphine)palladium (58.9 mg, 0.05 mmol) and sodium carbonate (164 mg, 1.55 mmol). The mixture was stirred at 90° C. under nitrogen atmosphere for 18 hours. Once the start material was consumed, the resultant mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=30:1) to give tert-butyl 4-(1-phenylvinyl)benzoate (0.59 g, 87.5percent). 1H NMR (300 MHz, CDCl3): delta 7.96 (d, J=4.8 Hz, 2H), 7.41-7.26 (m, 7H), 5.55-5.53 (m, 2H), 1.61 (s, 9H).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 29263-94-3, 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the compound of Reference Example 61 (176 g) in tetrahydrofuran (1000 ml) were addded tetrakistriphenylphosphine palladium (2.21 g) and morpholine (200 g), and the mixture was stirred at room temperature. Twenty-five minutes later, to the reaction solution were added a 5 % aqueous potassium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (156 g). To a solution of the obtained 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (138 g) in N,N-dimethylformamide (1000 ml) were added potassium carbonate (91 g), diethyl 2-bromo-2-methylmalonate (94 g), and the mixture was stirred at 80C for 8 hours. The reaction solution was allowed to cool to room temperature, filtered through celite, and to the filtrate were added a 5 % aqueous sodium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g). Subsequently, to a suspension of iron (110 g) in acetic acid (500 ml) was added dropwise a solution of the obtained diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g) in acetic acid (200 ml) slowly at 90C. Ten hours later, the mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to give the title compound (102 g). Rf = 0.25 (n-hexane/ethyl acetate=1/1)

The chemical industry reduces the impact on the environment during synthesis Diethyl 2-bromo-2-methylmalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP2447264; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics