Month: July 2021

Electric Literature of 3618-04-0, A common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 oxalyl chloride (6 mL, 68.8 mmol) in DCM (100 mL) at -78° C. was added dropwise a solution of DMSO (6.4 mL, 90 mmol) in DCM (20 mL). The mixture was stirred at this temperature for 15 min before the dropwise addition of a solution of ethyl 4-hydroxycyclohexane carboxylate (4.8 mL, 30 mmol) in DCM (20 mL). The mixture was stirred at -78° C. for 3 h before addition of TEA (29.3 mL, 210 mmol) in DCM (20 mL). The mixture was then gradually warmed to rt, washed with a sat. aq. NH4Cl solution and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography over SiO2 (Hex/EA 1:1) to give the title ketone (4.6 g, 90percent yield) as a colourless oil. 1H NMR (CDCl3) delta: 4.19 (q, J=7.1 Hz, 2H); 2.80-2.70 (m, 1H); 2.55-2.45 (m, 2H); 2.40-2.30 (m, 2H); 2.25-2.10 (m, 2H); 2.05-2.00 (m, 2H); 1.29 (t, J=7.1 Hz, 3H).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; US2009/105232; (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. 6290-49-9, name is Methyl 2-methoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-methoxyacetate

Reference Example 100 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanone [Show Image] To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole (2.20 g) in tetrahydrofuran (50 mL) was slowly added a 1.6M n-butyllithium hexane solution (9.6 mL) at -70C under a nitrogen atmosphere. The reaction mixture was stirred at -70C for 1 hr, and methyl methoxyacetate (2.91 g) was added. The reaction mixture was warmed to room temperature, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (2.00 g, yield 62%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 65-66C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6290-49-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 618-89-3,Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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 18(a)Methyl 3-{[5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-yl]amino}benzoate 5-Fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine (obtained from Example 1(b)) (99 mg, 0.42 mmol), methyl 3-bromobenzoate (97 mg, 0.45 mmol) and Cs2CO3 (230 mg, 0.71 mmol) were mixed in anhydrous 1,4-dioxane and the mixture was flushed with argon for 10 minutes before Pd2(dba)3 (23 mg, 0.025 mmol) and X-Phos (24 mg, 0.050 mmol) were added. The mixture was flushed with argon, then heated in a sealed tube at +90-100 C. until the reaction was complete. The reaction mixture was diluted with CH2Cl2, filtered and evaporated. The residue was taken up in CH2Cl2 and the organic phase was washed with H2O. Residual water was removed from the organic phase by treatment with Na2SO4. The crude of the base product was purified using preparative HPLC to give the title compound (97 mg, 62%) as a solid.1H NMR (400 MHz, DMSO-d6) delta ppm 9.73 (s, 1H) 8.57 (d, 1H) 8.19 (t, 1H) 8.04-7.95 (m, 1H) 7.59-7.52 (m, 1H) 7.43 (t, 1H) 7.37 (d, 1H) 5.44-5.31 (m, 1H) 3.84 (s, 3H) 2.51 (s, 3H) 1.42 (d, 3H) 1.40 (d, 3H); MS (ESI) m/z 370 (M+1).

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

Reference:
Patent; AstraZeneca AB; US2008/214560; (2008); 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. 103-41-3, name is Benzyl cinnamate, A new synthetic method of this compound is introduced below., Recommanded Product: Benzyl cinnamate

General procedure: Rh(Phebox-sb) 1b (2.8 mg, 0.0050 mmol), bis(pinacolato)-diboron (140 mg, 0.55 mmol), and NaOt-Bu (2.4 mg, 0.025 mmol) were placed in a flask with a stirring bar. Under an argon atmosphere, (E)-ethyl cinnamate 2a (88.1 mg, 0.50 mmol) and toluene (1.0 mL) were added. The mixture was stirred at 80 C for 0.5 h. At room temperature, the mixture was directly charged to a silica-gel column with an eluant of hexane/ethyl acetate to give the borylated product 3a in 86% yield (131 mg, 0.43 mmol). A part of the product (ca.0.2mmol) was subjected to the oxidation with sodium peroxoborate (5 equiv) in THF (1 mL) and H2O (1 mL) at room temperature for ca. 3 h to give the corresponding alcohol 4a. The enantioselectivity was determined by chiral chromatography to give 97% ee.

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:
Article; Toribatake, Kenji; Zhou, Li; Tsuruta, Ayae; Nishiyama, Hisao; Tetrahedron; vol. 69; 17; (2013); p. 3551 – 3560;,
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924-99-2, name is Ethyl 3-(dimethylamino)acrylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C7H13NO2

Step 8; The compound (85.17 g, 0.31 mol) obtained in Step 7 was dissolved in toluene (450 ml), thionyl chloride (44.40 ml, 0.61 mol) and dimethylformamide (catalytic amount) were added, and the mixture was stirred at 90C for 1 hr. After allowing to cool, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in toluene. The mixture was concentrated under reduced pressure, and this operation was repeated several times. The residue was dissolved in tetrahydrofuran (250 ml) and the obtained solution was added dropwise to a solution of ethyl 3-dimethylaminoacrylate (43.60 g, 0.31 mol) and triethylamine (50.90 ml, 0.37 mol) in tetrahydrofuran (200 ml) and the mixture was heated under reflux for 15 hr. After allowing to cool, water (300 ml) and ethyl acetate (500 ml) were added to the reaction mixture and the mixture was stirred and partitioned. The organic layer was washed with water (300 ml) and saturated brine in this order, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give a crude product (124.80 g) as a brown oil.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JAPAN TOBACCO INC.; WO2005/113509; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 144267-96-9,Some common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, molecular formula is C9H8F2O2, 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.

Following general procedure A, to 4-butylphenol (1.75 mL, 11.4 mmol) and K2CO3 [1-90 g, 13.8 mmol) in DMSO (18 mL) was added ethyl 3,4-difluorobenzoate (1.37 mL, 9 mmol) and the reaction was then stirred at 80 C for 24 hours in an argon atmosphere. The reaction was cooled to room temperature and quenched by the addition of water. The aqueous layer was extracted with EtOAc (3x). The combined organics were washed first with 1 M aqueous NaOH (1x) then washed with brine (1x), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 100% to 80% PE-DCM gradient to give the title compound as colorless oil (1.80 g, 63%).1H NMR (300 MHz, CDCI3) delta 7.84 (dd,j = 11.2, 2.0 Hz, 1H), 7.75 (ddd,/ = 8.5, 2.0, 1.2 Hz, 1H), 7.23 – 7.12 (m, 2H), 7.01 – 6.88 (m, 3H), 4.37 (q, / = 7.1 Hz, 2H), 2.67 – 2.55 (m, 2H), 1.68 – 1.52 (m, 2H), 1.46 – 1.23 (m, 5H), 0.94 ft, / = 7.3 Hz, 3H). 13C NMR (75 MHz, CDCI3) delta 165.4 (d, / = 2.6 Hz), 153.7, 153.0 (d,/ = 249.0 Hz), 149.5 (d,j = 11.2 Hz), 139.3, 129.9, 126.4 (d,/ = 3.5 Hz), 126.0 (d,j = 6.3 Hz), 119.0, 119.0 (d,/ = 1.4 Hz), 118.3 (d, J = 19.9 Hz), 61.3, 35.1, 33.8, 22.5, 14.4, 14.1. HRMS (C19H22F03+): expected: 317.1548; found: 317.1549.

The synthetic route of 144267-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REINMUeLLER, Viktoria; (121 pag.)WO2018/154118; (2018); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, molecular formula is C8H11NaO5, 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. Application In Synthesis of Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

Preparation of 6-hydroxy-2-phenylpyrimidine-4-carboxylic acid:; Diethyl oxaloacetate sodium salt 4.84 g (23.0 mmol) was added to a solution of 16 mL of water and 4 mL of ethanol. The suspension was stirred for 5 min, then a solution of 3.6 mL (22.5 mmol) of 6.25 M NaOH(O(? ) was added. The mixture was stirred at ambient temperature for 15 minutes to give a tan solution. To this was added a solution of 3.01 g (19.2 mmol) of benzamidine hydrochloride in 15 mL of H2O, giving a solution with pH=l 1. Next, 1 mL of 6.25 M NaOH was added, pH = 1 1 when done, then the reaction was stirred at 80 C for 2 h. Additional NaOH was added during the heating period to maintain the pH between 1 1 and 12. (A total of about 10 mmol additional NaOH was added.) The reaction was cooled to 5 C, then 12M HCl was added until pH = 1. The white precipitate was collected, washed with water, and dried on the filter to give 3.09 g (74%) of the product as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40876-98-0, its application will become more common.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2009/61453; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H7ClO4S

A solution of aniline (0.490 mL, 5.369 mmol) and pyridine (0.520 mL, 6.443 mmol) in dichloromethane (10 mL) was mixed at the room temperature with methyl 3-(chlorosulfonyl)propanoate (1.102 g, 5.906 mmol). The reaction mixture was stirred at the same temperature for 12 hr. Then, water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous 0. iN-hydrochloric acid solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The title compound was used without further purification (methyl 3-(N-phenylsulfamoyl)propanoate, 1.000 g, 71.3 %, brown solid).

According to the analysis of related databases, 15441-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 135484-83-2, 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. 135484-83-2, name is Methyl 2-amino-4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 2-amino-4-bromobenzoate (15 g, 65 mmol) in trifluoroacetic acid (75 mL) and concentrated HC1 (15 mL) was cooled in an ice water bath. To it sodium nitrite (9.0 g, 130 mmol) in water (15 mL) was added via addition funnel over 15 mm. The reaction stirred at 0 C for 30 mm. Then sodium azide (13 g, 196 mmol) was slowly addedportion-wise. The reaction was stirred at 0 C to rt for 1.5 hrs. The solvents were removed and H20 and EtOAc were added. The layers were separated and the organic layer was washed with saturated NaHCO3 three times and dried over Na2SO4. The solvent was removed and the crude material was purified by chromatography thru a Si02 using a solvent gradient of 100 % Hx to 20 % EtOAc / Hx to afford the title compound (16 g, 61mmol, 95 %). ?H NMR (400 MHz, CDC13) oe ppm 7.74 (d, J 8.4 Hz, 1H), 7.38 (d, J 1.8 Hz, 1H), 7.34 – 7.29 (m, 1H), 3.90 (s, 3H).

The synthetic route of Methyl 2-amino-4-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; KICK, Ellen, K.; BODAS, Mandar; MOHAN, Raju; BUSCH, Brett, B.; AVERBUJ, Claudia; VALENTE, Meriah; WURTZ, Nicholas; RAO, Prasanna Savanor, Maddu; SHETTY, Jeevanprakash; VENU, Alla; WO2014/152738; (2014); 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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, A new synthetic method of this compound is introduced below., Computed Properties of C6H9BrO2

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

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:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics