Month: December 2020

Synthetic Route of 35120-18-4, A common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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.

7-bromoquinoline-4-thiol 31b (220 mg, 0.90 mmol), ethyl 1-bromocyclobutanecarboxylate (227 mg, 1.10 mmol) and cesium carbonate (896 mg, 2.70 mmol) were added to 5 mL of NA-dimethylformamide, successively. The reaction solution was heated to 60 C. and stirred for 2 hours, then mixed with 50 mL of water, stirred uniformly, and extracted with ethyl acetate (50 mL*3). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with elution system C to obtain the title compound ethyl 1-((7-bromoquinolin-4-yl)thio)cyclobutanecarboxylate 31c (100 mg, a colorless oil) yield: 30%. MS m/z (ESI): 368.1 [M+1]

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; Shanghai Hengrui Pharmaceutical Co., Lt.d; PENG, Jianbiao; SUN, Piaoyang; LAN, Jiong; GU, Chunyan; LI, Xiaotao; LIU, Bonian; HAN, Chunzhou; HU, Qiyue; JIN, Fangfang; DONG, Qing; CAO, Guoqing; (57 pag.)US2016/108035; (2016); A1;,
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Electric Literature of 124-06-1, 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. 124-06-1, name is Ethyl tetradecanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Example 4) Synthesis of N-[2-(1-methylpyrrolidin-2-yl)ethyl]myristamide (Compound 4) toluene (1.00 ml), dried using MS 4A, was mixed with 1.00 ml of a n-hexane solution of 15% Me3Al. With the mixture being cooled in an ice-methanol bath, 0.17 ml (0.78 mmol) of 2-(2-aminoethyl)-1-methylpyrrolidine was added dropwise over about 2 minutes.. After stirring for 20 minutes, the temperature was raised to room temperature, and 0.5 ml of a toluene solution of 0.2 g (0.78 mmol) of myristic acid ethyl ester was added dropwise over 1 minute.. After stirring for 2 hours at 70C, the mixture was cooled with ice, and a 1N NaOH solution was added dropwise.. The mixture was stirred for 10 minutes, and water and ethyl acetate were added.. Then, the mixture was separated into respective layers, and the organic layer was washed twice with 20 ml of a saturated aqueous solution of sodium chloride.. After this layer was dried over anhydrous magnesium sulfate, it was concentrated under reduced pressure on a 30C water bath to obtain the captioned compound (yield 0.25 g).. This compound was subjected to silica gel column chromatography (mobile phase: CHCl3:MeOH (19:19:1)) for purification. NMR and mass spectrum confirmed the purified compound to have the following structure:

The synthetic route of Ethyl tetradecanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Maruha Corporation; EP1408030; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 115913-32-1, 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. 115913-32-1, name is Dimethyl bicyclo[1.1.1]pentane-1,3-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

50 Ml three-mouth bottle added 1.48 g bicyclo [1.1.1] pentane – 1, 3 – dicarboxylic acid dimethyl ester, its use 20 ml methanol dissolved, slowly dropping NaOH at room temperature (324 mg) in methanol (5 ml) solution, after adding up to 80 C reaction 2 h. After the reaction is finished concentrated to dry, add 40 ml water, dichloromethane is used for extraction (50 ml * 3), the water layer to adjust the PH dilute hydrochloric acid, adding dichloromethane extraction (40 ml * 4), the combined organic layer, drying the concentrated white solid 925 mg, yield 68%.

The synthetic route of Dimethyl bicyclo[1.1.1]pentane-1,3-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Bai Li Pharmaceutical Co., Ltd.; Zhu Yi; Li Jie; Liu Weijia; Wan Weili; Zhuo Shi; (26 pag.)CN109180681; (2019); A;,
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These common heterocyclic compound, 4492-02-8, name is Ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate, 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. Formula: C10H14N2O2

Example 1 IndazoLe-3-Carboxylic Acid A mixture of 4,5,6,7-tetrahydroindazole-3-carboxylic acid ethyl ester (21.0 g, 108 mmol), 5% palladium on carbon (7.0 g solid, 3.29 mmol of Pd), and 210 mL of cymene was heated to reflux for 38 hours. At this point complete conversion to the indazole-3-carboxylic acid ethyl ester was shown by TLC (silica gel, 3:1 ethyl acetate-heptane). The reaction was cooled to 120 C. and the 5% palladium on carbon was removed by filtration.

The synthetic route of Ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US5914405; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 151583-29-8, name is Methyl 3-(3-bromophenyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H11BrO2

Example 37B: 3-(3-methoxy-3-oxopropyl)phenylboronic acid j00413j DMSO (6.86 mL) and dioxane (6.86 mL) were degassed for 15 mm bybubbling with argon. Meanwhile, Example 37A (400 mg, 1.645 mmol), KOAc (404 mg,4.11 mmol), and bis(neopentyl glycolato)diboron (520 mg, 2.304 mmol) were placed in amicrowave tube. To these compounds was added the degassed solvents. The tube was sealed and degassed for an additional 15 mi [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (135 mg, 0.165 mmol) was subsequently added, the tubesealed, and heated to 90 C and allowed to stir overnight. The reaction was diluted withEtOAc and washed twice with brine, dried (Na2SO4), filtered, and concentrated in vacuo.The crude reaction mixture was purified by Prep LC (Axia Luna 5 t Cl 8 3 Ox 100 mmcolumn, 10 mm gradient from 40 to 100% B in A, A = 10:90:0.1 MeCN:H20:TFA, B =90:10:0.1 MeCN:H20:TFA) to yield Example 37B (O.224g, 64%) which was usedimmediately after purification.

The synthetic route of 151583-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); A1;,
Ester – Wikipedia,
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Related Products of 541-16-2, 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 541-16-2 as follows.

Compound 168 (80 mg, 0.14 mmol) was dissolved in 10 mL of acetonitrile and iodomethane (86 [mu] L, 1.39 mmol) was added and reacted at room temperature for 24 hours.The reaction solution is directly concentrated,The compound 168 was rinsed with a 50 mL mixture of petroleum ether: dichloromethane = 4: 1 (v / v)Of the imidazole moiety of iodomethane salt 75 mg, yield 76%; A tryptamine (2.0 g, 12.5 mmol) was dissolved in 20 mL of tetrahydrofuran,(3.5 mL, 25 mmol) and tert-butoxycarboxylic anhydride (3.03 g, 15.0 mmol) were added in turn followed by reaction at 10 C for 1 hour,The reaction solution was poured into 100 mL of ice water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, concentrated by flash column chromatography, and eluted with petroleum ether: ethyl acetate = 2: 1 (v / v) to give N- [2- (3-indole) ethyl] carbamic acid tert-butyl ester, yield 97%;A solution of tert-butyl N- [2- (3-indole) ethyl] carbamate(1.8 g, 6.92 mmol) was dissolved in 110 mL of THF / H2O (10: 1)Down to 0 C,DDQ (3.1 g, 13.8 mmol) was added and reacted at this temperature for two hours.The reaction solution was poured into 200 mL of ethyl acetate and washed with saturated sodium bicarbonate solution to a colorless color,The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The column was separated by flash column chromatography,Petroleum ether: ethyl acetate = 1: 1 (v / v)2- [3-oxo-2- (3-indole) ethyl] carbamate in a yield of 63%A solution of tert-butyl N- [2-oxo-2- (3-indole) ethyl] carbamate (200 mg, 0.73 mmol)Treated with 5 mL of trifluoroacetic acid, reacted at 10 C for one hour,Benzene (5 mL x 3 times) was obtained by azeotropic removal of trifluoroacetic acidN- [2-oxo-2- (3-indole) ethyl] trifluoroacetic acid in 185 mg, yield 93%.(75.0 mg, 0.105 mmol) of the imidazole moiety of compound 168 was dissolved in 2 mL of DMF and triethylamine (73.0 [mu] L, 0.525 mmol) and N- [2-oxyadienyl-2- (3-indole(85.4 mg, 0.315 mmol, 3.0 equiv) was added and reacted at room temperature for 24 hours.The reaction solution was diluted with 10 mL of ethyl acetate, washed with 1N hydrochloric acid,Dried over anhydrous sodium sulfate and concentrated.Semi-preparative HPLC separation, MeOH: H2O = 9: 1 (v / v)Eluting to give 40 mg of 3′-N- [N- (2-oxo-2- (3-indolyl) ethyl) aminothioformyl] staurosporine (169) in 56% yield.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

36692-49-6, name is Methyl 3,4-diaminobenzoate, 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. Product Details of 36692-49-6

A mixture of (4-tert-butyl-phenoxy)acetic acid (300 mg, 1.4 mmol), 3,4-diaminobenzoic acid methyl ester (300 mg, 1.4 mmol) in PPSE (4.8 mL) was heated at 160 C. for 4 h. At the end of the reaction period, the mixture was taken to ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer was separated and the aqueous solution extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane=1:9-4:6) to afford 2-2,4-tert-butyl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (547 mg, 80% yield). 1H-NMR (CDCl3, 300 MHz) 8.39 (1H, s, aromatic), 8.03 (1H, d, J=8.1 Hz, aromatic), 7.66 (1H, d, J=7.8 Hz, aromatic), 7.27 (2H, d, J=8.4 Hz, aromatic), 6.88 (2H, d, J=8.7 Hz, aromatic), 5.43 (2H, s, OCH2), 3.95 (3H, s, OCH3), 1.27 (9H, s, t-butyl), NH not detected.

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

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (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. 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H17NO2

46.4 g (200 mmol) of 4-chloro-1,8-naphthalic anhydride and 41.4 g (200 mmol) of tert-butyl 4-aminomethylbenzoate were placed in 250 mL of EtOAc to form a suspension.Stir at RT for 16 hours.The resulting precipitate was filtered and dried at 50 C for 8 hours.A white powder of 48 g (yield 57%) was obtained.

According to the analysis of related databases, 107045-28-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Institute of Biophysics, Chinese Academy of Sciences; Suzhou Shoutong Science And Technology Co., Ltd.; Dai Yu; Zhao Jianyong; Zhang Wenxin; (21 pag.)CN108675989; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6933-47-7,Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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.

Synthesis 184-(3,5-Dichloro-4-ethoxybenzamido)-2-methylbenzoic acid (AAA-019)Step (i): Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3)1A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2- methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCI (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3 x 15 mL), dried over MgS04, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2- methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)” (ES”). 1H NMR (400 MHz, CDCI3) delta: 7.97 (1 H, s), 7.80 (3H, m), 7.54 (1 H, dd), 7.51 (1 H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; CORCORAN, Jonathan Patrick Thomas; KALINDJIAN, Sarkis Barret; BORTHWICK, Alan David; ADAMS, David Reginald; BROWN, Jane Theresa; TADDEI, David Michel Adrien; SHIERS, Jason, John; WO2011/27106; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 20372-66-1, A common heterocyclic compound, 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, molecular formula is C8H5F3O2, 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.

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals; 950.61 mg; 5 mmol; 1 eq.), sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) and tetrabutylammonium bromide (2 014.82 mg; 6.25 mmol; 1.25 eq.) were dissolved in DMF (10 mL) . The resulting mixture was heated at 6O0C overnight. As the reaction was not complete, sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) was added and the mixture was stirred at 6O0C for additiona 24 h. The resulting dark pink solution was diluted with EtOAc and washed with brine several times. It was dried over MgSO4, filtrated and evaporated, resulting into a sticky dark red oil, which was purified by flash chromatography (Sitheta2 100 g, EtOAc / c-hex 1 :9 until 1 :1 ), affording the title product. 1H NMR (DMSO-d6, 300 MHz) delta 7.77 (dd, J = 5.45, 8.41 Hz, 1 H), 7.42 (dd, J = 4.99, 8.88 Hz, 1 H), 3.96 (s, 3H). LC/MS (Method A): 463.2 (M-H)”; 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

The synthetic route of 20372-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics