Author: Jessica.F

Application of 4897-84-1, A common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, molecular formula is C5H9BrO2, 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 solution of the methyl ester (XIV, 1.8 g, 0.15 mmol) in DMF (50 mL), is added 4-bromo-butyric acid methyl ester (1 g, 0.87 mmol) and Cs2CO3 (800 mg, 0.48 mmol). The reaction is stirred at 22° C. for 48 hours. 5 g SiO2 is added to the mixture and all solvents were evaporated in vacuo. The solid is purified by flash chromatography, eluting with MeOH/DCM (0-10percent) to provide 1.5 g (75percent), of a yellow solid. MS m/z 1357 (M +H2O).

The synthetic route of 4897-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bushell, Simon; LaMarche, Matthew J.; Leeds, Jennifer; Whitehead, Lewis; US2009/156628; (2009); 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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H14ClNO2

Description 169: methyl 4-(1-(5-chloro-2-(3-((2,4- difluorophenyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate (D169)A mixture of 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1 -yl)nicotinic acid (D1 18) (40 mg, 0.1 18 mmol), 1 -Hydroxybenzotriazole hydrate (18 mg, 0.1 18 mmol) and 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34 mg, 0.177 mmol) in dimethylformamide (5ml) was stirred 10 min at room temperature. A solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (32.2 mg, 0.141 mmol) and triethylamine (0.02ml, 0.141 mmol) in dry dimethylformamide (2ml) was added and the mixture was stirred 24h at room temperature. After solvent evaporation, water (10ml) was added and the formed precipitate was filtered off and purified by Biotage SNAP-Si (1 Og) cartridge eluting with a mixture dichloromethane/methanol from 100/0 to 80/20. Collected fractions, after solvent evaporation afforded the title compound (D169) (105 mg).MS: (ES/+) m/z: 513.2 [MH+] C26H23CIF2N403 requires 512.141 H NMR (400MHz ,DMSO-d6) delta = 9.23 (s, 1 H), 8.21 (d, J = 2.4 Hz, 1 H), 7.91 – 7.80 (m, J = 8.3 Hz, 2 H), 7.74 (d, J = 2.4 Hz, 1 H), 7.40 – 7.29 (m, J = 8.3 Hz, 2 H), 7.18 – 7.06 (m, 1 H), 6.85 (t, J = 8.6 Hz, 1 H), 6.48 (d, J = 5.4 Hz, 1 H), 6.03 (br. s., 1 H), 4.22 (d, J = 3.9 Hz, 3 H), 3.86 (s, 3 H), 3.76 (d, J = 4.9 Hz, 2 H), 1 .34 (d, J = 9.3 Hz, 4 H)

According to the analysis of related databases, 1014645-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Application In Synthesis of tert-Butyl 4-bromobutanoate

[000730] To a solution of Example 1.2.7 (0.103 g) and tert-butyl 4-bromobutanoate (0.032 g) in dichloromethane (0.5 inL) was added N,N-diisopropylethylamine (0.034 mL) at 50 C in a sealed amber vial overnight. The reaction was concentrated, dissolved in dimethyl sulfoxide/methanol (1 : 1, 2 mL) and purified by reverse phase HPLC using a Gilson system, eluting with 5-75% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. MS (ESI) m/e 944.6 (M+l).

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

Reference:
Patent; ABBVIE INC.; TAO, Zhi-Fu; DOHERTY, George; WANG, Xilu; SULLIVAN, Gerard M.; SONG, Xiaohong; KUNZER, Aaron R.; WENDT, Michael D.; MARIN, Violeta L.; FREY, Robin R.; CULLEN, Steve C.; WELCH, Dennie S.; SHEN, Xiaoqiang; BENNETT, Nathan B.; HAIGHT, Anthony R.; ACKLER, Scott L.; BOGHAERT, Erwin R.; SOUERS, Andrew J.; JUDD, Andrew S.; (623 pag.)WO2016/94509; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, 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 15964-79-1, COA of Formula: C11H14O4

Manufacturing Example 13: Preparation of 2-(3,4-Dimethoxyphenyl) acetaldehyde (52) Anhydrous diethyl ether solution containing methyl 3′,4′-dimethoxyphenyl acetate (1.94 g, 9.24 mmol) was stirred, during which DIBAL-H (11.1 mL, 1 M in THF solution) was added thereto drop by drop with maintaining the temperature at -78C. The mixture was stirred at the same temperature for 1 hour. Rochelle aqueous solution was carefully added thereto for 15 minutes. The mixture of the two phases was stirred vigorously at 0 C for 1 hour, which was added to water. The water layer was extracted with EtOAc (*2) and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the compound 52 of Manufacturing Example 13 (yield: 68%, 1.13 g). 1H NMR (CDCl3, 300 MHz) delta 9.66 (t, 1H, J = 2.5 Hz), 6.80 (d, 1H, J = 8.0 Hz), 6.68 (m, 1H), 6.64 (d,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; SNU R&DB Foundation; SUH, Young-Ger; CHANG, Dong-Jo; AN, Hongchan; KIM, Kyu-Won; KIM, Young-Myeong; LEE, Ho-Young; EP2871187; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2×20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
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Electric Literature of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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: A solution of the 4 (0.48 g, 2 mmol), 3-fluoroaniline (0.24g,2.2 mmol) in isopropanol (30 ml) were stirred at 90 C for 4 h.Isopropanol was removed under reduced pressure and the residuewas purified through a column chromatography on silica withchloroform/methanol (V:V 50:1) as a white solid (0.58 g, 91.8percentyield).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Huai-Wei; Deng, Cheng-Long; Li, Dan-Dan; Liu, Dan-Dan; Chai, Shao-Meng; Wang, Wei; Zhang, Yan; Chen, Kai; Li, Xin; Wang, Jian; Song, Shao-Jiang; Song, Hong-Rui; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 460 – 470;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 33993-24-7,Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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.

A mixture of 20 g (136 mmol) 1 ,3,5-triazine-2,4-diamine hydrochloride (GAS-No of free base:504-08-5), 500 mL water and 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was stirred for 1 day at RT. 20 g (130 mmol) cyclopropanecarbonylcyclopropanecarboxylate was added into the reaction and stirring was continued for 1 day at room temperature. Another batch of 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was added and stirring was continued for 3 days at room temperature. The above procedure was repeated once and the solutions of two batch reaction were combined. The solids were filtered off and the crude product purified by FlashPrep-HPLC (column: 018 silica gel; mobile phase, ACN/water (0.05% NH4OH) =5% increasing to ACN/water (0.05% NH4OH)=20% within 12 mm; Detector, UV 254 nm) to give10.5 g (22%) of the title compound.LC-MS: m/z = 180 [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 Cyclopropanecarboxylic anhydride, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
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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 59833-69-1 as follows. 59833-69-1

General procedure: To a stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
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Related Products of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: 3-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 muL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRADSHAW, Curt W.; Sakamuri, Sukumar; Fu, Yanwen; Oates, Bryan; Desharnais, Joel; Tumelty, David; US2009/98130; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, molecular formula is C10H17NO2, 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. HPLC of Formula: C10H17NO2

At RT, 258 mg (1.41 mmol) of methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 402 mg (1.06 mmol) of HATU and 182 mg (1.41 mmol) of DIPEA were added to a solution of 210 mg (0.71 mmol) of 6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid in 5 ml of DMF. The mixture was then stirred at 60 C. for 1 h. After cooling to RT, the mixture was added to 20 ml of a 10% strength citric acid solution. The resulting precipitate was filtered off, washed with water and dried under reduced to pressure. This gave 326 mg (97% of theory, purity 98%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.48 (s, 1H), 8.05 (d, 1H), 7.77 (dd, 1H), 7.66 (d, 1H), 7.60-7.47 (m, 5H), 3.59 (s, 3H), 2.32 (s, 3H), 2.09-2.00 (m, 6H), 1.91-1.82 (m, 6H). LC/MS (Method 1, ESIpos): Rt=1.22 min, m/z=463 [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 135908-33-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEININGHAUS, Mark; TERJUNG, Carsten; MUENSTER, Uwe; OLENIK, Britta; (92 pag.)US2018/36300; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics