Tag: M.W=100-200

Synthetic Route of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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.

Compound 1-8A mixture of Inter mediate-2 (15 mg, 1 equiv.) and methyl 1-hydroxycyclopropanecarboxylate (14 mg, 3 equiv.) in THF was cooled to -78 C. Contents were treate with sodium hydride (5.3 mg, 60% suspension in mineral oil, 3 equiv.) and warmed to 23 C and stirred for 18 h. The contents were concentrated in vacuo, and the residue was purified via silica gel chromatography utilizing a 0-30% ethyl acetate/hexanes gradient to deliver the desired compound (16 mg, 84%>) as a white solid. 1H-NMR (500 MHz, CDCb) delta 8.47 (s, 2 H), 7.23-7.17 (m, 1 H), 7.16 (s, 1 H), 7.02 (t, 1 H), 6.98 (t, 1 H), 6.93-6.88 (m, 1 H), 6.58 (s, 1 H), 5.95 (s, 2 H), 3.70 (s, 3 H), 1.76-1.71 (m, 2 H), 1.45-1.40 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-hydroxycyclopropanecarboxylate, its application will become more common.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; RENNIE, Glen Robert; PERL, Nicholas; LEE, Thomas Wai-Ho; RENHOWE, Paul Allan; NAKAI, Takashi; MERMERIAN, Ara; IM, G-Yoon Jamie; (235 pag.)WO2016/44445; (2016); A2;,
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Related Products of 952285-52-8, A common heterocyclic compound, 952285-52-8, name is Methyl 4-amino-2,5-difluorobenzoate, molecular formula is C8H7F2NO2, 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.

(Step 1) Synthesis of methyl 2,5-difluoro-4-[(4-nitrophenyl)sulfonylamino]benzoate A 4-nitro benzene sulfonyl chloride (8.9 g, 40.1 mmol) was added to a pyridine solution (30 ml) of methyl 4-amino-2,5-difluoro-benzoate (3.0 g, 16.0 mmol), followed by stirring at 50?C for 18 hours. The resultant mixture was concentrated under reduced pressure, and the residue was slurry washed using acetonitrile to obtain methyl 4-[bis[(4-nitrophenyl)sulfonyl]amino]-2,5-difluoro-benzoate (11.6 g).

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; EA Pharma Co., Ltd.; TOKUMASU Munetaka; NOGUCHI Masatsugu; KAWAHIRA Mizuki; IWASAKI Kana; HAYAKAWA Nobuhiko; MIYANAGA Wataru; SAITOU Yuki; YAMAURA Yui; ANDO Ayatoshi; TSURUTA Atsushi; NOGUCHI Misato; (127 pag.)EP3412660; (2018); A1;,
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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. Safety of Ethyl 3-(dimethylamino)acrylate

220g of toluene, 95g of triethylamine, 200g acid chloride sequentially into the acylation reactor, open stirring, cooling to 13 ;Preparation of the first 98g N, N-dimethylamino ethyl acrylate added to the dropping device, keeping the reaction kettle temperature 12 open stirring dropping,25 minutes to complete all the dropwise addition is completed, slowly heated to 75 C and incubated for 6 hours; step is completed, cooled to20 C, into 60g L-aminopropanol, slowly heated to 45 C, incubated for 3 hours, was added 200g saturated brine,Slowly add dropwise adjust PH5.5, stirring for 20 minutes, retest PH value after stopping stirring Stirred stratification, toluene layer decompression recovery of tolueneNo toluene solution into the reactor, pumped DMF200g stirring dissolved into the ring reactor high tank to be used; to the reaction within the reactorInto DMF1500g, start stirring, cast KF130g, temperature and pressure before recovery fraction to the reactor temperature 160 . Add amineThe reaction solution was heated to maintain refluxing heat 4 hours; end of the insulation, cooling to below 100 , DMF was recovered under reduced pressureWill be dry. After the end of the recovery of high pure water 1200g, stirred for 40 minutes, filtered, washed with water, finally rinsed with methanol, dried, too176g product, 96.8% molar yield.

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

Reference:
Patent; Yancheng Xin’an Zhou Pharmaceutical Co., Ltd.; Chen Chengle; Zhang Wenbiao; (6 pag.)CN106565745; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate, 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 46004-37-9, Product Details of 46004-37-9

Methyl-2-chloro-4-(methylsulfonamido) benzoate (101).; To a stirred solution of methyl-2-chloro-4-amino benzoate 100 (0.457 g, 2.45 mmol) in DCM cooled to 0 0C was added pyridine (2 mL) followed by dropwise addition of methanesulphonyl choride (0.2 mL, 2.5 mmol). After addition was complete, the reaction was allowed to warm to room temperature and stirred for 2 h. After completion, the reaction mixture was concentrated in vacuo. 1 N HCl (5 mL) was added to the residue and the mixture extracted with EtOAc (10 mL). The organic phase was dried over Na2SO4 and concentrated under high vacuum. The crude compound was purified by column chromatography to afford the title intermediate 101 as a solid (0.54 g, 84% yield).

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 4-amino-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; CANNE BANNEN, Lynne; CHAN, Diva Sze-ming; GU, Xiao-hui; MAC, Morrison, B.; NG, Stephanie; WANG, Tie-lin; WANG, Yong; XU, Wei; WO2010/65760; (2010); A1;,
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Electric Literature of 443-26-5, These common heterocyclic compound, 443-26-5, name is Ethyl 2-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.

O-fluorobenzoic acid (5g, 35.7mmol) was dissolved in 20mL of ethanol, a catalytic amount of concentrated sulfuric acid was added dropwise, and the mixture was stirred at reflux overnight. After the reaction was completed, the ethanol was rotated.Extracted with ethyl acetate (25 mL ¡Á 3),The organic phase is combined, washed with saturated sodium hydrogen carbonate solution, washed with saturated brine and dried over anhydrous sodium sulfate.Concentrated to give a colorless oily productEthyl fluorobenzoate 4.9g;Ethyl fluorobenzoate (4.9 g, 29.1 mmol) was dissolved in 20 mL of DMSO, and morpholine (12.7 mL, 145.7 mmol) was added dropwise and stirred at 120 overnight.After the reaction, ethyl acetate was extracted (25 mL¡Á3), and the organic phase was combined, washed with water (25 mL¡Á3),After concentration, the oily product was 4.5 g;The above product (4.5 g, 19.1 mmol) was dissolved in 10 mL of methanol.Add 10 mL of 10% aqueous NaOH solution.After stirring at 80 C for 2 h, the methanol was rotated, and the pH was adjusted to 4 with 10% dilute hydrochloric acid.Solid precipitated and filtered to obtain 3.2 g of 2-morpholinylbenzoic acid.Three-step yield of 43.2%;The o-fluorobenzoic acid (50 mg, 0.24 mmol) was obtained in the same manner as in Example 1 to obtain 45g, two-step yield 54.9%of the product.

The synthetic route of 443-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Xu Jinyi; Li Wenlong; Xu Shengtao; Shuai Wen; Xu Feijie; Sun Honghao; Ma Cong; Zhu Zheying; Yao Hong; (35 pag.)CN109678815; (2019); A;,
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These common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, 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. Recommanded Product: Ethyl 3,4-difluorobenzoate

Cesium carbonate (8.3 g, 25.4 mmol) was added to a mixture of 3-hydroxy-5-{[(1S)-2- hydroxy- 1 -methylethyl]o’xy) -N-( I -methyl- lH-pyrazol-3-yl)benzamide (3.7 g, 12.7 mmol) and ethyl-3,4-difluorobenzoate (2.36 g, 12.7 mmol) in dimethylacetamide (60 mL) and the stirred mixture heated at 115C for 3 hours. The mixture was allowed to cool to RT and ethyl acetate (100 mL) added. The mixture was washed with water (5 x 40 mL), brine (40 mL), dried (MgS04), filtered, and reduced in vacuo. The residue was chromatographed on silica, eluting with 50% ethyl acetate in isohexane, to give the desired compound (1.8 g). ?H NMR No. (CDC13): 1.31 (d, 3H), 1.41 (t, 3H), 3.72 (d, 2H), 3.83 (s, 3H), 4:39 (q, 2H), 4.57 (sex, 1H), 6.75 (m, 1H), 6.83 (m, 1H), 7.09 (m, 2H), 7.30 (d, 2H), 7.83 (m, 2H), 8.91 (brs, 1H). m/z 458(M+H)+

The synthetic route of Ethyl 3,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/121110; (2005); A1;,
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Synthetic Route of 294190-18-4, The chemical industry reduces the impact on the environment during synthesis 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, I believe this compound will play a more active role in future production and life.

Step 1 : Synthesis of methyl 3-(((trans)-4-((tert-butoxycarbonyl) amino) cyclohexyl) amino)-5-chloro-2-methylbenzoate: [0910] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (100 g, 502 mmol) and tert-butyl (4-oxocyclohexyl) carbamate (160.5 g, 753 mmol) in dichloroethane (1 L), acetic acid (180.9 g, 3015 mmol) was added and the reaction was stirred at rt for 30 min. Then sodium triacetoxyborohydride (319.5 g, 1507 mmol) was added at 0 C and the reaction was stirred at rt for 16 h. The progress of the reaction was monitored by TLC. Upon completion; the reaction was quenched with aqueous sodium bicarbonate, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography (100-200 mesh size) eluting with 2, 4, 6 & 8% ethyl acetate in hexane to remove maximum cis isomer. This afforded 120 g of mixture of cis and trans isomers (40:60 by HPLC). The trans isomer was purified by repetitive recrystazlisation with ethyl acetate: hexane (1 :2) to afford 65 g of pure trans isomer (65 g, 33%).

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 3-amino-5-chloro-2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 144267-96-9, 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. 144267-96-9, name is Ethyl 3,4-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 3,4-difluorobenzoate (1 .5 g) in N,N-dimethylformannide (15 mL) 1 ,2,4-triazole (1 .1 g) and K2CO3 (2.3 g) are added and the mixture is heated at 150 C in a microwave for 30 min. After cooling, water and ethyl acetate are added and the organic layer is dried over MgSO4 and concentrated. The residue is purified by chromatography on silica gel eluting with 0% to 100% ethyl acetate/hexane. The pure ester is dissolved in methanol (30 mL) and 4 M aqueous NaOH solution (3 mL) is added and the mixture is stirred at room temperature for 1 h. The mixture is neutralized with 6 M hydrochloric acid, concentrated, and then acidified with 6 M hydrochloric acid, and the precipitate is filtered off washing with a small amount of water and dried by suction to give the acid as a white solid.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,4-difluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; NOSSE, Bernd; BLUM, Andreas; HECKEL, Armin; HIMMELSBACH, Frank; ASHWEEK, Neil J.; HARRIOTT, Nicole; WO2014/37327; (2014); A1;,
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Reference of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

Chloro(1 ,1-dimethylethyl)dimethylsilane (115g; 0.76mol) was added in portions over 1 hour to a solution of ethyl 4-hydroxycyclohexanecarboxylate (118g; 0.68mol), imidazole(103g; 1.52mol) and dimethylformamide (400ml) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to~40C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2L) and extracted with diethyl ether (2 x 800ml). The ether extracts were washed with water, brine and then dried (Na2SO4) and the solvent was removed to give the title compound as a oil (198.4g) 1H NMR delta (CDCI3, 400 MHz): 0.01 (6H, m), 0.85 (9H, s), 1.2 (3H, m), 1.3-1.5 (2H, m), 1.6 (2H, m), 1.85-2 (3H, m), 2.15-2.3 (1 H, m) 3.5 (0.4H, m) 3.86 (1 H, m) 4.1 (1 H, m).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107565; (2007); 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. 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7F2NO2

methyl 2-amino-4,5-difluorobenzoate (40.0 g, 214 mmol) and NCS (25.9 g, 194 mmol) were suspended in DMF (10 mL) and heated at 95 C. for 30 min. Water and DCM were added to the mixture. The organic phase was separated. The aqueous phase was extracted with DCM (2 x 10 mL). The combined organic phases were dried, filtered and concentrated. The resulting residue was purified by normal phase chromatography (0 to 40% EtOAc in hexanes) to give compound 148a (11 g, 26% yield) as a white solid.

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 207346-42-7.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXO GROUP LIMITED; YAMAWAKI, KENJI; YOKOO, KATSUKI; SATO, JUN; KUSANO, HIROKI; AOKI, TOSHIAKI; LIAO, XIANG MIN; PEARSON, NEIL DAVID; PENDRAK, ISRAIL; THALGI, REEMA; (373 pag.)JP6377570; (2018); B2;,
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