Esters-buliding-blocks

Reference of 69812-51-7, 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. 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of cytisine (2 mmol) in dichloromethane (30 mL), triethylamine (2.4 mmol), and 4-methoxycarbonyl benzenesulfonyl chloride (2.2 mmol) were added and stirred at room temperature until the TLC analysis showed completion of the reaction. Then the reaction solution was washed with water and brine. The organic phase was dried with anhydrous sodium sulfate and concentrated to give a residue, which was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent and then acidified with 2 N HCl/Et2O to give the title compounds. Yield: 85%; white solid; mp: 112-114 C. 1H NMR (600 MHz) delta 7.73 (t, J=6.0 Hz, 1H), 7.68-7.62 (m, 2H), 7.59 (d, J=7.2 Hz, 1H), 7.36 (dd, J=8.4, 7.2 Hz, 1H), 6.24 (d, J=8.4 Hz, 1H), 6.18 (d, J=6.0 Hz, 1H), 3.84 (s, 1H), 3.81 (s, 3H), 3.78-3.70 (m, 2H), 3.65-3.64 (m, 1H), 3.19 (s, 1H), 2.92-2.81 (m, 2H), 2.52 (s, 1H), 1.85-1.78 (m, 2H); 13C NMR (151 MHz) delta 168.2, 162.5, 150.1, 139.5, 134.4, 133.5, 133.4, 131.2, 128.9, 128.6, 116.6, 105.2, 53.3, 53.1, 52.1, 49.0, 33.8, 26.8, 24.3. HRMS: calcd for C19H21N2O5S [M+H]+ 389.1166, found: 389.1155.

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-chlorosulfonylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tang, Sheng; Li, Yinghong; Bao, Yunyang; Dai, Zhiting; Niu, Tianyu; Wang, Kun; He, Hongwei; Song, Danqing; Bioorganic Chemistry; vol. 90; (2019);,
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Reference of 1150566-27-0,Some common heterocyclic compound, 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, molecular formula is C9H8ClN3O2, 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.

[0418] Step 1. 6- [(5-Fluoro-2-hydroxy-benzyl)-methyl-amino] -imidazo [1 ,2-b]pyridazine-3- carboxylic acid ethyl ester (42B). To a mixture of 4-fluoro-2-methylaminomethyl-phenol (20L, 305.2 mg, 1.97 mmol) and 6-chloro-imidazo [1 ,2-b]pyridazine-3-carboxylic acid ethyl ester (42A, 230 mg, 1.02 mmol) in DMSO (5 mL) was added KF (180 mg, 3.01 mmol). The reaction mixture was stirred at 120 C for 18 hours under nitrogen. The solution was then cooled to ambient temperature, diluted with water (20 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were further washed with water (3 x 50 mL) and brine (50 mL), dried over Na2504 and concentrated. The residue was then purified by a silica gel column eluting with EtOAc/hexane (0-50%, 10 CV) to afford the desired product as a white solid (240 mg, 69%). LC-MS (ESI) m/z 345.2 (M+H) ?H NMR (500 MHz, chloroform-d) oe 8.61 (s, 1H),8.17 (s, 1H), 7.91 (d, J= 10.0 Hz, 1H), 7.00-6.86 (m, 4H), 4.78 (s, 2H), 4.47 (qd, J= 7.2, 0.5 Hz, 2H), 3.17 (s, 3H), 1.41 (td, J= 7.1, 0.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, its application will become more common.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
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Electric Literature of 66315-16-0, The chemical industry reduces the impact on the environment during synthesis 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, I believe this compound will play a more active role in future production and life.

1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid methyl ester may be prepared from 3-amino-4-methylamino-benzoic acid methyl ester, 2-amino-6-(trifluoromethoxy)benzothiazole, 1,1?-thiocarbonyl-diimidazole, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). 1,1?-Thiocarbonylimidazole may be added to a solution of 2-amino-6-(trifluoromethoxy)benzothiazole in DMF, and the reaction mixture stirred at 90-100 C. for a day. To this reaction mixture at room temperature is added EDC and stirred at 60 C. for 5 min. To this reaction mixture at room temperature is added 3-amino-4-methylamino-benzoic acid methyl ester and stirred at 90 C. The reaction mixture may then be cooled to room temperature, poured into ice-cold water and the solid collected by filtration. The crude product thus obtained may be purified by trituration with dichloromethan-methanol (9:1). LC/MS: m/z 423.8 (M+1)+.

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-4-(methylamino)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; vTv Therapeutics LLC; Kassis, Jareer Nabeel; Attucks, Otis Clinton; Kostura, Matthew J.; (41 pag.)US2017/56413; (2017); A1;,
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Electric Literature 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.

To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NAOH solution (92.4 g in 185 mL H20) was added 1,2- dibromobutane (30.0 g, 138.9 mmol) and DI-TERT-BUTYLMALONATE (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred 18 h at rt, a mixture of ice and water was then added. The crude product was extracted with CH2CI2 (3x) and sequentially washed with water (3x), brine and the organic extracts combined. The organic layer was dried (MgS04), filtered and concentrated in vacuo. The resulting residue was flash chromatographed (100 G SI02, 3% ET20 in hexane) to afford the titled product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99316; (2003); A1;,
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Synthetic Route of 17435-72-2, 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. 17435-72-2, name is Ethyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 6 Synthesis of ethyl 2-Phenoxymethylacrylate A solution of ethyl 2-bromomethylacrylate (2.00 g, 10.4 mmol, ref: Villieras, J. and Rambaud, M. Synthesis, 1982, 914) and phenol(975 mg, 1.0 eq) in dry THF (20 ML) under N2 at 0 C. was treated with anhydrous K2CO3 (1.43 g, 1.0 mol eq).. No reaction was observed for 1 h.. anhydrous DMF (20 ML) was added and stirred for 2 h at 0 C. and for 1 h at room temperature.. After evaporation of DMF, water(100 ML) was added, and the reaction was extracted with ethyl acetate (100 ML*2).. The organic extract was washed with brine (100 ML), dried (anh. Na2SO4), filtered and concentrated.. Flash chromatography (40% CH2Cl2/hexanes) gave 1.712 g (80%) of the title compound. 1H-NMR (500 MHz, CDCl3) delta 7.30 (2H, yt, J=7.3 Hz), 6.99-6.96 (3H, m), 6.41 (1H, s), 6.01 (1H, s), 4.78 (2H, s), 4.27 (2H, q, J=7.33 Hz).

The synthetic route of Ethyl 2-(bromomethyl)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem Investment Ltd.; US6747050; (2004); B1;,
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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 23680-40-2 as follows. SDS of cas: 23680-40-2

Methyl 3-bromopropiolate (1 13 g, 698 mmol) and freshly cracked cyclopentadiene (92 g, 1 .39 mol) were dissolved in toluene (570 ml_) and heated to 90 C, under nitrogen for 2 hr. The reaction was cooled to room temperature, and the toluene evaporated in vacuo to give a dark brown oil. This was azeotroped three times with acetonitrile to remove excess dicyclopentadiene, giving the title compound (1 19 g, 74% yield) as a brown oil. 1 H NMR (400 MHz, CDCI3) delta ppm 6.88 – 6.94 (m, 1 H), 6.85 (ddd, J = 5.2, 3.1 , 1 .0 Hz, 1 H), 4.00 (dqd, J = 2.8, 1 .7, 0.8 Hz, 1 H), 3.76 (s, 3 H), 3.69 (ddtd, J = 3.2, 2.4, 1 .5, 0.7 Hz, 1 H), 2.32 (dt, J = 6.7, 1 .7 Hz, 1 H), 2.13 (dt, J = 6.7, 1 .7 Hz, 1 H).

According to the analysis of related databases, 23680-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BURNS, Aaron Craig; COLLINS, Michael Raymond; GREASLEY, Samantha Elizabeth; HOFFMAN, Robert Louis; HUANG, Qinhua; KANIA, Robert Steven; KUNG, Pei-Pei; LINTON, Maria Angelica; NARASIMHAN, Lakshmi Sourirajan; RICHARDSON, Paul Francis; RICHTER, Daniel Tyler; SMITH, Graham; WO2015/166373; (2015); A1;,
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Synthetic Route of 178312-47-5,Some common heterocyclic compound, 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, molecular formula is C9H14F2O2, 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 solution ofbutyllithium(2.000 mL, 2.80 mmol) was added to a cold (-78 C.) solution ofdiisopropylamine(0.396 mL, 2.80 mmol) inTHF(5 mL) under N2and the mixture was stirred at -78 C. for 1 h. A solution ofethyl 4,4-difluorocyclohexanecarboxylate(384 mg, 2 mmol) in THF (2 mL) was added at -78 C. and the mixture was stirred for 1 h and then gradually warmed to -20 C. over 2 h and then re-cooled to -78 C. Neat((chloromethoxy)methyl)benzene(0.226 mL, 2.200 mmol) was added and the mixture was allowed to warm to rt over 2 h. The reaction was quenched with satd. NH4Cl and extracted with EtOAc and washed with water, brine, dried (Na2SO4). Evaporation of the solvent afforded a lightyellowoil which was purified by silica gel FCC (1:1 DCM-hexanes) to afford1-((benzyloxy)methyl)-4,4-difluorocyclohexanecarboxylateas acolorlessoil.

The synthetic route of 178312-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); A1;,
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3196-23-4, name is Methyl 1-bromocyclohexanecarboxylate, 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. COA of Formula: C8H13BrO2

To a suspension of chromium (II) chloride (1. 00 g, 8. 10 MMOL) and lithium iodide (0. 087 G, 0. 648 MMOL) in tetrahydrofuran (20 mL) was added 4- [2- (5-METHYL-2- phenyl-1, 3-oxazol-4-yl) ethoxy] BENZALDEHYDE (Preparation 1) (1. 00 g, 3. 24 MMOL) and methyl 1-bromocyclohexanoate (1. 07 g, 4. 85 MMOL). The resulting mixture was heated at 50 C until TLC analysis indicated the reaction was complete. The mixture was cooled to ambient temperature and satuarted aqueous sodium chloride (15 mL) was added. The resulting mixture was stirred for 15 minutes, then partitioned between water and ethyl acetate. The organic phase was washed with water and dried (anhydrous magnesium sulfate), filtered and evaporated. The residue was purified by flash column chromatography (hexanes to 50% ethyl acetate/hexanes) to yield the title compound as a colorless oil (0. 797 G, 55%). LRMS (M/Z) : 450 (M+H).

The synthetic route of 3196-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/92145; (2004); A1;,
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Related Products of 91367-05-4, 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 91367-05-4 as follows.

To a solution of methyl 4-chloro-3-methylbenzoate (2.22 g, 12 mmol) in CCl4 (16 mL) was added NBS (2.35 g, 13.2 mmol) and AIBN (0.031 g, 0.19 mmol) and the reaction was refluxed for 3 h. After cooled down, the reaction was filtered and the filtrate was washed with H2O, dried over N yi 3H), 4.628 (s, 2H,), 7.494 (d, IH, /=8.4 Hz), 7.942 (d, IH, /=8.4 Hz), 8.143 (s, IH).

According to the analysis of related databases, 91367-05-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/65093; (2007); A2;,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 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.

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 924-99-2.

Reference:
Patent; Yancheng Xin’an Zhou Pharmaceutical Co., Ltd.; Chen Chengle; Zhang Wenbiao; (6 pag.)CN106565745; (2017); A;,
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