Month: June 2021

Some common heterocyclic compound, 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, molecular formula is C8H12O2, 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: C8H12O2

Formation of Methyl-1-methylcyclohex-2-ene-1-carboxylate (66a) (2554) To a cold (0 C.) solution of freshly distilled N-isopropylpropan-2-amine (4.20 mL, 29.96 mmol) in THF (150 mL) under argon was added dropwise nBuLi (12.65 mL of 2.2 M solution, 27.82 mmol). After 15 min the solution was cooled to 78 C. and dry HMPA (4.84 mL, 27.82 mmol) was added. The mixture was stirred for 30 min at 78 C. and methyl cyclohexene-1-carboxylate (3.00 g, 21.40 mmol) was then added. After stirring an additional 10 min, methyl iodide (2.00 mL, 32.10 mmol) was added. The solution was then allowed to warm to 5 C. over 2 h. An aqueous saturated solution of NH4Cl was poured into the orange mixture. After dilution with hexanes and washing with brine, the organic layer was dried over Na2SO4 and carefully evaporated to 3.3 g of generate methyl 1-methylcyclohex-2-ene-1-carboxylate, 66a, which was used without further purification. (2555) 1H NMR (300 MHz, CDCl3) delta 5.77 (dt, J=10.1, 3.5 Hz, 1H), 5.66 (s, 1H), 3.71-3.58 (m, 3H), 2.16 (ddd, J=12.9, 7.0, 3.4 Hz, 1H), 2.03-1.88 (m, 2H), 1.72-1.53 (m, 2H), 1.49-1.37 (m, 1H), 1.32-1.14 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18448-47-0, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Charifson, Paul S.; Clark, Michael P.; Bandarage, Upul K.; Bethiel, Randy S.; Court, John J.; Deng, Hongbo; Davies, Ioana; Duffy, John P.; Farmer, Luc J.; Gao, Huai; Gu, Wenxin; Jacobs, Dylan H.; Kennedy, Joseph M.; Ledeboer, Mark W.; Ledford, Brian; Maltais, Francois; Perola, Emanuele; Wang, Tiansheng; Wannamaker, M. Woods; Byrn, Randal; Zhou, Yi; Lin, Chao; Jiang, Min; Jones, Steven; Germann, Ursula A.; Salituro, Francesco G.; Kwong, Ann Dak-Yee; (411 pag.)US9345708; (2016); B2;,
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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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H13BrO2

General procedure: BuLi (1.6 M in hexane, 1.45 equiv) was added to a stirred solution of 3 in THF (0.022 M) at -78 C and the resultant mixture was stirred at -78 C for 1 h. The requisite electrophile was added and the resultant mixture was stirred at -78 C for 10 min, then MeOH was added. The reaction mixture was concentrated in vacuo and the residue was extracted with CH2Cl2, then filtered through basic alumina (grade V) and purified by flash column chromatography on basic alumina (grade I) to give 28-30.

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 39149-80-9.

Reference:
Article; Bashiardes, George; Bodwell, Graham J.; Collingwood, Stephen P.; Costello, James F.; Davies, Stephen G.; Fletcher, Ai M.; Garner, Alan; Preston, Simon C.; Thomson, James E.; Tetrahedron; vol. 70; 46; (2014); p. 8938 – 8951;,
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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. 110661-91-1, name is tert-Butyl 4-bromobutanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H15BrO2

Exemplification of General Procedure J:; Preparation of teri-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-l/7- indol-l-yl)butanoate; To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(lH-indol-4-yl)-l,2,4-oxadiazole (0.100 g, 0.283 mmol) in DMF (0.999 mL) was added NaH (0.012 g, 0.311 mmol). After about 15 min tert- butyl 4-bromobutanoate (0.095 g, 0.424 mmol) was added and the reaction mixture was heated to about 50 C. After about 24 h the reaction mixture was cooled to ambient temperature, concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-lH-indol-l- yljbutanoate (0.135 g, 93%) as a colorless oil that solidified on standing. LC/MS (Table 1, Method c) Rt = 3.50 min, m/z 496 (M+H)+.

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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Reference of 36692-49-6,Some common heterocyclic compound, 36692-49-6, name is Methyl 3,4-diaminobenzoate, molecular formula is C8H10N2O2, 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 suspension of methyl 3,4-diaminobenzoate (10.0 g, 60.2 mmol) and N-hydroxyethanimidamide (10.6 g, 95 % purity, 135 mmol) in dioxane (20 mL) was addedcaesium carbonate (19.6 g, 60.2 mmol) and the mixture was stirred at 110 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (sodium sulfate), filtered and the solvent was removed in vacuum to give a solid that was triturated with methanol to give 8.00 g (70 % yield) of the title compound.LC-MS (Method 2): R1 = 0.67 mm; MS (ESIpos): m/z = 191 [M+H]1H-NMR (400 MHz, DMSO-d6)oe [ppm]: 2.308 (16.00), 4.831 (2.74), 5.429 (3.11), 6.583 (2.69),6.603 (2.81), 7.148 (1.50), 7.153 (1.72), 7.169 (1.30), 7.174 (1.62), 7.212 (3.04), 7.217 (2.53).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,4-diaminobenzoate, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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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. 13195-64-7, name is Diisopropyl malonate, A new synthetic method of this compound is introduced below., Formula: C9H16O4

Example 1Preparation of Protected Diester 2 The dihydroisoquinoline 1 (1.0 eq.) and Boc anhydride (1.5 eq.) were dissolved in CH2Cl2 at room temperature to provide a 1.5 M solution with respect to the dihydroisoquinoline. The mixture was allowed to stir for 30 min. Following the allotted time, the reaction mixture was cooled to 0° C. and then diisopropylmalonate (1.5 eq.) followed by a pre-chilled solution of the Pd catalyst (0.008 eq.) in dichloromethane were added successively to the reaction mixture to provide a final reaction concentration of 0.84 M with respect to the starting dihydroisoquinoline. The reaction mixture was allowed to continue stirring at 2.5° C. for 15 h. Following this time EtOAc and brine were added to the reaction mixture. The aqueous layer was extracted with three portions of EtOAc and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the crude product. The crude material was dissolved in a minimal amount of dichloromethane and purified by flash chromatography on SiO2 (15-30percent EtOAc-hexanes, elution was observed at 285 nm and 228 nm). The product 2 was a colorless solid that existed as a mixture of rotamers in solution at room temperature 94percent: [alpha]26D -69.0 (c 0.21, CHCl3); 1H NMR (CDCl3) delta 0.81-1.02 (m, 6H), 1.06-1.17 (m, 6H), 1.23-1.38 (m, 9H), 2.51-2.63 (m, 1H), 2.64-2.77 (m, 1H), 3.20-3.29 (m, 0.6H), 3.32-3.41 (m, 0.4H), 3.51-3.58 (m, 1H), 3.62-3.70 (m, 6H), 3.70-3.76 (m, 0.4H), 3.91-4.01 (m, 0.6H), 4.65-4.82 (m, 1H), 4.83-4.98 (m, 1H), 5.71 (apparent d, J=5.7 Hz, 0.6H), 5.78 (apparent d, J=7.9 Hz, 0.4H), 6.42-6.49 (m, 1H), 6.77 (s, 0.6H), 6.81 (s, 0.4H); 13C NMR (CDCl3) delta 21.02, 21.09, 21.18, 21.32, 27.24, 27.95, 28.02, 37.60, 39.34, 52.11, 52.83, 55.48, 55.52, 59.28, 60.08, 68.58, 68.76, 68.82, 79.46, 80.03, 110.09, 110.73, 111.13, 126.11, 126.18, 126.37, 127.07, 146.81, 146.87, 147.93, 153.86, 154.30, 166.29, 166.78, 166.94, 167.06.

The synthetic route of 13195-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENERAL ELECTRIC COMPANY; US2008/306269; (2008); A1;,
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Application of 924-99-2, 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows.

a) Ethyl 2-[2,5-difluorobenzoyl]-3-dimethylamino-2-propenoate; A solution of 2,5-difluorobenzoyl chloride (5.26 g) in toluene (100 mL) was treated with ethyl-3-dimethylamino-2-propenoate (5.27 g), followed by triethylamine (5.9 mL). The mixture was stirred at 90C for 6.5 h then allowed to cool, and the precipitate removed by filtration. The filtrate was concentrated in vacuo to give a residue which was purified by flash chromatography (silica gel, 50-100% Et2O in petroleum ether [b.p. 40-600C]) to give the title compound as a yellow oil (0.95 g); ESMS m/z 284.2 [M+H]+, 306.1 [M+ Na]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3-(dimethylamino)acrylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); A1;,
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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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 36692-49-6

Example 21: 3-Amino-6-{4-[2-hydroxy-2-(2-phenyl-lN-benzoimidazol-5-yl)- ethylamino]-piperidin-1-yl}-4-propyl-thieno [2, 3-b] pyridine-2-carboxylic acid amide 0 0 o H i I so) Hunig’s base N -ire NH DCM 0 NH2 NH2 acetic acid H H THF / N N H min02 Mn02 N THE zon H 21 3,4-Diamino-benzoic acid methyl ester (2 g, 12.035 mmol) was dispersed in 40 mL DCM. Added hunig’s base (2.516 mL, 14.442 mmol) and stirred at RT until everything was in solution. Added benzoyl chloride (1.397 mL, 12.035 mmol) dropwise into the mixtuxe and stirred at RT for 1 hour. Added sat. NaHC03 aq. solution into the reaction mixture. Extracted with DCM three times. Combined all organic extracts and washed with brine. Dried over Na2SO4. Filtered and removed solvent in vacuo. Purified by flash chromatography using 10 % MeOH/DCM as eluent mixtures. 4-Amino-3-benzoylamino- benzoic acid methyl ester was trituated in hot ethyl acetate and 1.667 g (51.2 %) white solid was obtained.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/56562; (2005); A1;,
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Application of 94994-25-9, A common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, molecular formula is C11H16O3, 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 stirred solution of methyltriphenylphosphonium bromide (9.1 g, 12.8 mmol) in THF (50 ml) at 0 C. was added potassium hexamethyldisilazide (0.5M in toluene, 48.6 ml), dropwise over 5 min. The resulting mixture was allowed to warm up to room temperature over 1 h, then cooled again to 0 C. and treated with methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate 15-A (Chapman, N. B. et al. J. Org. Chem., 1970, 35, 917) (2.5 g, 12.8 mmol). The reaction mixture was stirred at room temperature for 18 h then diluted with EtOAc (350 ml). The organic phase was washed with aqueous HCl (1 N), saturated aqueous sodium bicarbonate, and brine, then dried (Na2SO4) and concentrated in vacuo. The resulting solid was purified by flash silica gel chromatography, eluting with a gradient 0-4% EtOAc/hexanes. The resulting methyl 4-vinylbicyclo[2.2.2]octane-1-carboxylate 15-B was isolated as a clear, colorless 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; Waddell, Sherman T.; Santorelli, Gina M.; Maletic, Milana M.; Leeman, Aaron H.; Gu, Xin; Graham, Donald W.; Balkovec, James M.; Aster, Susan D.; US2004/133011; (2004); A1;,
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Electric Literature of 924-99-2, 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

ffl-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(l-hvdroxy-3J-dimethylbutan-2- ylamino)acrylate.To a solution of 2,6-difluoro-5-iodonicotinic acid (4 g, 14.04 mmol, 1 equiv.) in toluene (30 mL) was added thionyl chloride (5.12 mL, 70.18 mmol, 5 equiv.) followed by DMF (0.5 mL). The reaction was stirred at 110 0C for 1 h. The reaction was concentrated. The residue was re-suspended in THF (15 mL) and added dropwise to a solution of ethyl-3- (dimethylamine)acrylate (2.1 mL, 14.04, 1,1 equiv.) and triethylamine (2.15 mL, 15.44 mmol, 1.1 equiv.) in THF (15 mL). The reaction was stirred at 67 0C for 2 h and cooled to 23 C. (5)-2-amino-3,3-dimethylbutan-l-ol (1.81 g, 15.44 mmol, 1.1 equiv.) was subsequently added and stirred at 23 0C for 30 min. The reaction was quenched with water (40 mL) and ethyl acetate (40 mL). The aqueous layer was extracted with ethyl acetate (2×40 mL), and the organics were dried and concentrated. The compound was purified via silica gel chromatography and concentrated to provide (5)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(l- hydroxy-3,3-dimethylbutan-2-ylamino)acrylate Intermediate 80 (4.49 g, 66 %). Calcd for C17H21F2IN2O4 [M + H]+: 482.9.

The synthetic route of Ethyl 3-(dimethylamino)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIFULCO, Neil; CHOY, Allison, Laura; QUIROGA, Olga; SHERER, Brian; WO2010/136817; (2010); A1;,
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Related Products of 6279-86-3, The chemical industry reduces the impact on the environment during synthesis 6279-86-3, name is Triethyl methanetricarboxylate, I believe this compound will play a more active role in future production and life.

p-Methoxyaniline (123 mg, 1 mmol) was dissolved in dimethylformamide (1 ml).;Then, triethyl methanetricarboxylate (232 mg, 1 mmol) was added.;The mixture was heated for six hours at 170-190 C. The reaction was cooled to rt and treated with ethanol, filtered and washed with ethanol to yield 8 as a yellow solid (143 mg, 58%); mp 308-310 C; 1H NMR (500 MHz, DMSO-d6) delta 3.79 (s, 3H), 3.86 (s, 3H), 7.01 (d, J = 8.9 Hz, 2H), 7.40 (br s, 3H), 7.59 (d, J = 8.9 Hz, 2H), 12.01 (s, 1H), 12.63 (s, 1H), 16.67 (s, 1H); 13C NMR (125.7 MHz, DMSO-d6) delta 55.09, 55.38, 96.39, 104.22, 114.13, 114.51, 117.33, 122.13, 123.65, 129.58, 133.11, 154.53, 156.26, 161.98, 168.39, 171.37; Anal. for C18H16N2O5: Calcd C, 63.52; H, 4.74; N, 8.23. Found C, 63.66; H, 5.00; N, 8.09.

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, Triethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sabbah, Dima A.; Simms, Neka A.; Wang, Wang; Dong, Yuxiang; Ezell, Edward L.; Brattain, Michael G.; Vennerstrom, Jonathan L.; Zhong, Haizhen A.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7175 – 7183;,
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