Month: March 2021

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. 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 5-amino-2-chlorobenzoate

89.1 2-Chloro-5-(6-chloro-pyridazin-3-ylamino)-benzoic acid methyl ester A solution of 3,6-dichloropyridazine (240 mg) and methyl-5-amino-2-chlorobenzoate (299 mg) in EtOH (9 mL) was heated in the microwave for 30 min at 150 C. The reaction was concentrated in vacuo and the crude was purified by CC (Hept/EtOAc 1/0 to 4/6) to give 203 mg of the titled compound as a light yellow solid. LC-MS (B): tR=0.72 min; [M+H]+: 298.06

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; US2014/73651; (2014); A1;,
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Reference of 1459-93-4,Some common heterocyclic compound, 1459-93-4, name is Dimethyl isophthalate, molecular formula is C10H10O4, 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.

3-Ethynylaniline (3) (0.6 mL, 5.6 mmol) was dissolved in THF (15 mL) in the presence of n-butyllithium (1.6 M in hexane, 3.5 mL, 5.6 mmol) and the mixture was stirred at -78 C for 30 min, then dimethyl isophthalate (4) (1 g, 5.15 mmol) was added dropwise to the mixture and the solution was stirred overnight under N2. After removing solvent by evaporation, the crude product was purified by recrystallization from methanol to obtain 5 (1.3 g, 4.65 mmol, 90%). 1H NMR (300 MHz, DMSO-d6) delta 8.60 (s, 1H), 8.21 (m, 2H), 7.90 (m, 1H), 7.74 (d, J = 8.13 Hz, 1H), 7.66 (t, J = 7.80, 7.80 Hz, 2H), 7.37 (t, J = 7.88, 7.88 Hz, 1H), 7.28 (d, J =7.69 Hz, 1H), 3.97 (s, 3H), and 3.52 (s, 1H) ppm. 13C NMR (75 MHz, DMSO-d6) delta 166.24, 165. 32, 135.76, 134.33, 133.85, 132.62, 131.03, 130.43, 128.75, 128.44, 126.21, 126.02, 122.11, 121.78, 84.12, 83.78, and 50.07 ppm. ESI-MS m/z: Observed 278.25 [M-H]-, [M-H]- calcd = 278.09.

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

Reference:
Article; Choi, Yeonweon; Jung, Sung Ho; Lee, Areum; Seo, Moo Lyong; Jung, Jong Hwa; Bulletin of the Korean Chemical Society; vol. 36; 6; (2015); p. 1725 – 1728;,
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Synthetic Route of 61644-18-6, A common heterocyclic compound, 61644-18-6, name is Chloromethyl isobutyrate, molecular formula is C5H9ClO2, 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 9 Preparation of (Z)-(N’-(2,6-dimethylphenyl)-N-(2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropyl)-carbamimidoylthio)methyl isobutyrate (Compound 15) To a solution of 1-(2,6-dimethylphenyl)-3-(2-(4-(1-(4-(trifluoromethoxy)-phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropyl)thiourea (75 mg, 0.143 mmol) in chloroform (CHCl3; 0.72 mL) was added chloromethyl isobutyrate (31.1 mg, 0.172 mmol). The mixture was heated at 100 C. for 1 h. The mixture was cooled to 25 C., and the residue was purified by silica gel chromatography (EtOAc-hexanes gradient) to afford the title compound (17.3 mg, 19%) as a yellow oil: IR vmax 3332 (br), 3124, 2976, 2939, 1739, 1631, 1590, 1518, 1264, 1171, 986 cm-1; 1H NMR (400 MHz, CDCl3) delta 8.54 (s, 1H), 8.09 (d, J=8.3 Hz, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.37 (d, J=8.3 Hz, 2H), 7.20 (d, J=7.2 Hz, 2H), 7.02 (d, J=7.5 Hz, 2H), 6.88 (t, J=7.5 Hz, 1H), 5.65 (br s, 2H), 2.88 (br s, 1H), 2.68-2.52 (m, 1H), 2.10 (s, 6H), 1.82-1.46 (m, 2H), 1.46-1.22 (m, 2H), 1.22-1.18 (m, 6H); ESIMS m/z 624 (M+H).

The synthetic route of 61644-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; Crouse, Gary D.; Lambert, William T.; Sparks, Thomas C.; Hegde, Vidyadhar B.; US2012/202688; (2012); A1;,
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Related Products of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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.

[0714] To a solution of 6.0 g (24 mmol) OF 2-HYDROXY-5-IODOBENZALDEHYDE and 5 mL (33.3 mmol) of ethyl 4,4, 4-trifluorocronate in 20 mL of dry DMF at 60 C was added potassium carbonate in one portion. The mixture was stirred at 60 C overnight. After cooling to room temperature, the solid was filtered and washed with EtOAc. The combined filtrates were diluted by addition with 300 mL EtOAc and washed with brine. The organic phase was dried over anhydrous magnesium sulfate and evaporated to afford an oil, which was further purified silica gel chromatography with EtOAc/hexane (1: 9). Concentration of the desired fractions afforded 4.7 g (49%) of a light yellow solid : H NMR (CDCL3/300 MHz) 7.65-7. 55 (m, 3H), 6.78 (d, J=8. 4Hz, 1H), 5.72 (q, J=6. 6 Hz, 1H), 4.34 (m, 2H), 1.37 (t, J=6. 9 Hz, 3H). MS (ES+) 398.9 (M+H, 100).

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

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Application of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-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.

tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125 C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;; ; Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); A1;,
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Synthetic Route of 816-27-3, These common heterocyclic compound, 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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.

A mixture of cis-l-amino-4-((tert-butyldimethylsilyl)oxy)-5-phenylpyrrolidin-2-one (9.0 g, 29.4 mmol) and ethyl 2-ethoxy-2-imino-acetate (21.3 g, 146.8 mmol) in toluene (500 mL) was heated at 90 C for 18 h and concentrated under reduced pressure. The residue was diluted with water (200 mL) and extracted with ethyl acetate (3 x 150 mL). The combined organic layers were concentrated under reduce pressure to afford crude ethyl cis-2-((3-((tert-butyldimethylsilyl)oxy) -5-oxo-2- phenylpyrrolidin-l-yl)amino)-2-iminoacetate (10.0 g, 84%) as a brown oil. LC-MS RT= 1.128 min, m/z = 406.4 [M + H]+. LCMS (10 to 80% acetonitrile in water + 0.03% trifluoacetic acid over 2.0 in, ESI+ found [M+H] = 406.4.

Statistics shows that Ethyl 2-ethoxy-2-iminoacetate is playing an increasingly important role. we look forward to future research findings about 816-27-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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Reference of 7686-78-4,Some common heterocyclic compound, 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, molecular formula is C11H16O4, 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.

Preparation method: In air atmosphere,Add 0.2 mmol of N-pyrimidindolline compound to the microwave reaction tube,0.36 mmol of ethylene cyclopropane compound,0.008mmol of [Ru (p-cymene) Cl2] 2,0.08 mmol mesitylene,0.04mmol of silver hexafluoroantimonate, microwave reaction at 60 C for 1 hour;After completion of the reaction, rinse with ethyl acetate.Chromatographic separation after concentration under reduced pressure (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to 100/0)Dried to a pale yellow oil,Yield: 81%, E / Z> 20: 1.

The synthetic route of 7686-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Henan Communication Polytechnic College; Zhu Xinju; Wang Qiuling; Xie Xiaona; Zhang Xiaojie; Yan Jing; Xu Yan; Hao Xinqi; Song Maoping; (15 pag.)CN110551106; (2019); A;,
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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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Recommanded Product: 35179-98-7

To a solution of ((R)-3~benzyloxycarbonylamino-2-hydroxy- EPO propyO-cyclohexylmethyl-phosphinic acid (1.0 g, 2.71 mmol) and carbonic acid chloromethyl ester ethyl ester (1.13 g, 8.16 mmol) in toluene (60 mL) was added silver carbonate (2.26 g, 8.16 mmol). The reaction mixture was heated at reflux for 3h. The reaction mixture was then filtered and was concentrated in vacuo. Purification by gradient flash chromatography (methanol/methylene chloride) on a 35 g RediSep disposable column gave (3- benzyloxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid ethoxycarbonyloxymethyl ester (300 mg, 0.63 mmol). 1H-NMR(CDCl3, 300 MHz): delta 7.35 (m, 5H), 5.65 (m,2H), 5.45 (br s, IH), 5.10 (s, 2H), 4.2 (m, 2H), 3.45 (dd, IH), 3.20 (dd, IH), 2.01-1.55 (m, HH), 1.40-0.95 (m, 8H).

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/86734; (2006); A1;,
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Reference of 26759-46-6, 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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 11 Benzoic acid, 2,2′-dithiobis[4,5-dimethoxy-, dimethyl ester To a suspension of methyl 2-amino-4,5-dimethoxy-benzoate (1.50 g, 7.11 mmol) in acetic acid (10 mL) and conc. HCl (13 mL) at an internal temperature of 1¡ã-3¡ã C. was slowly added a solution of sodium nitrite (0.55 g, 7.97 mmol) in water (5 mL); the solid went into solution upon the final addition of the aqueous sodium nitrite. The solution was stirred for an additional 30 minutes. and then sulphur dioxide was bubbled through the cold solution for 30 minutes. Cupric chloride dihydrate (0.471 g, 2.76 mmol) in water (5 mL) was added and the green mixture allowed to warm to room temperature over 48 hours. Filtration and washing with water (3*100 mL) afforded the required product as a white solid (0.800 g, 49percent). Analysis calc’d for C20 H22 O8 S2: C, 52.85; H, 4.88; Found: C, 52.64; H, 4.89. MS (CI) m/e 454.

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; Warner-Lambert Company; US5599811; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 957207-58-8, name is Methyl 4-bromo-2-(trifluoromethyl)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 957207-58-8, COA of Formula: C9H6BrF3O2

To a solution of methyl 4-bromo-2-(trifluoromethyl)benzoate (537 mg, 1.67 mmol) in 13 mL of toluene was added at room temperature cyclopropylboronic acid (220 mg, 2.56 mmol), K3PO4 (641 mg, 3.02 mmol), water (0.4 mL) and Pd(Ph3)4 (193 mg, 0.167 mmol) and the resulting mixture was degassed for 10 minutes with a stream of N2. The reaction mixture was stirred at 110 C for 7 hours. Water was added and product was extracted with ethyl acetate (three times). The collected organic layers were dried over Na2SO4, filtered and evaporated in high vacuum to yield methyl 4-cyclopropyl-2-(trifluoromethyl)benzoate (crude, 802 mg) as agrey solid. MS found for C12H11F3O2 as (M+H)+ 245.0.

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

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
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