Month: June 2021

Synthetic Route of 426831-32-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 426831-32-5, name is (5-Fluoro-2-methoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To 43 (1 eq, 17.9 mmol, 2.8 g) in CHCU (18 ml_) at room temperature, added HBr (22 mL) and the reaction mixture was stirred 2h, then diluted with dichloromethan, washed with water then brine, dried over sodium sulfate, and concentrated in vacuo to give 44 (3.3 g) as an off-white solid.

According to the analysis of related databases, 426831-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; BOGEN, Stephane, L.; MA, Yao; WANG, Yaolin; LAHUE, Brian Robert; NAIR, Latha, G.; SHIZUKA, Manami; VOSS, Matthew Ernst; KIROVA-SNOVER, Margarita; PAN, Weidong; TIAN, Yuan; KULKARNI, Bheemashankar, A.; GIBEAU, Craig, R.; LIU, Yuan; SCAPIN, Giovanna; RINDGEN, Diane; DOLL, Ronald, J.; GUZI, Timothy, J.; HICKLIN, Danny, J.; NOMEIR, Amin; SEIDEL-DUGAN, Cynthia; SHIPPS, Gerald, W., Jr.; MACCOSS, Malcolm; WO2011/46771; (2011); A1;,
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Related Products of 112-27-6 , The common heterocyclic compound, 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol, molecular formula is C6H14O4, 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.

Triethylenc glycol (17.5 mL, 19.7 g, 131.13 mmol. 5 eq) was dissolved in DCM (150 mL·} and trimethyiamine (5.48 mL, 3.98 g, 1.5 eq) and cooled to 0. TsCI (5.00 g, 26.23 mmol 1 eq) was then added and die reaction mixture stirred at room temperature tor 18 hours. The reaction was diluted into DCM and washed with water (3x) and brine (lx). The organic layer was dried over sodium sulfate and concentrated in. vacuo. The crude product was purified on silica (0-5% MeOH in DCM) to give compound 64 (6,89 g, 22,6 mmol) in 85% yield. lH NMR (400 MHz, Chloroform-t/) 6 7.80 (d, J – 8.3 Hz, 2H), 7.38 ~ 7.30 (m, 2H)S 4.23 4.14 (m, 2H), 3.71 (id, J = 5.3, 4.3 Hz, 4H), 3.66 – 3.55 (m, 6H), 2.45 (s, 3H). C NMR (101 MHz, cdcl3) 144.98, 133.09, 129,95, 128.09, 72.58, 70.91 , 70.44, 69.28, 68.84, 1.88, 2 /76.

The synthetic route of 112-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; SPIEGEL, David; CAIANIELLO, David; (247 pag.)WO2019/199621; (2019); A1;,
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Electric Literature of 558-42-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, molecular weight is 108.5667, as common compound, the synthetic route is as follows.

To a solution of 4-hydroxy-3,5-dimethylbenzonitrile (2.00 g, 13.5 mmol) and 1-chloro-2-methyl propan-2-ol (8.85 g, 81.5 mmol) in ethanol (50 mL) was added potassium carbonate (7.5 g, 54 mmol) and water (5 mL). The reaction EPO mixture was stirred at reflux for 24 hours. Cooled to room temperature. The precipitated solid was filtered off and washed with water. The solid was dissolved in ethyl acetate (100 mL), washed with water (50 mL), brine (50 ml_) and dried over anhydrous Na2SO4. Removal of solvent gave 4-(2-hydroxy-2- methylpropoxy)-3,5-dimethyl benzonitrile (2.9 g, 97percent) as a white solid. To a solution of 4-(2-hydroxy-2-methylpropoxy)-3,5-dimethyl benzonitrile (2.90 g, 13.2 mmol) in anhydrous DMF (20 mL) was added imidazole (2.7 g, 40 mmol) and tert- butyldimethylsilylchloride (2.19 g, 14.6 mmol). The reaction mixture was stirred at room temperature under nitrogen for 3 days. Water (200 mL) was added and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), and dried over anhydrous Na2SO4. The solventwas removed under reduced pressure and the crude compound was purified by column chromatography (Silica Gel 230-400 mesh; 10percent ethyl acetate in hexanes as eluent) to give 4-[2-(te/?-butyldimethylsilanyloxy)-2-methylpropoxy]- 3,5-dimethylbenzonitrile (2.24 g, 54percent). n-Butyl lithium (6.2 mL, 6.6 mmol, 1.6 M solution in hexanes) was added to a solution of 2,4-dimethoxy-6-/V- dimethylbenzamide (0.9 g, 4.3 mmol) in anhydrous THF (10 mL) dropwise at – 1O0C over a period of 10 min under nitrogen. The stirring was continued at O0C for 1 hour. The reaction mixture was cooled to -5O0C. A solution of 4-[2-(tert- butyldimethylsilanyloxy)-2-methylpropoxy]-3,5-dimethylbenzonitrile (1.58 g, 4.73 mmol) in anhydrous THF (5 mL) was quickly added. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The stirring was continued at room temperature for 1 hour. Aqueous ammonium chloride solution (10 mL) was added. Ethyl acetate (100 mL) was added. The organic layer was separated, washed with water (10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and the crude compound was purified by column chromatography (Silica Gel 230-400 mesh; 0-5percent methanol in CH2CI2 as eluent) to give 3-{4-[2-(terf-butyldimethylsilanyloxy)-2-methylpropoxy]- 3,5-dimethylphenyl}-6,8-dimethoxy-2H-isoquinolin-1-one (0.82 g, 37percent) of as white solid. The above compound (0.42 g, 0.82 mmol) was dissolved in anhydrous THF (20 mL). Tetrabutyl ammonium fluoride (4.1 mL, 1.0M solution in THF) was added at O0C. The reaction mixture was stirred at O0C for 10 min, then at room temperature for 2 h and then stirred at 7O0C for 24 hours. The mixture was cooled EPO to room temperature. Saturated aqueous ammonium chloride (30 ml_) was added. The organic phase was separated, washed with water, brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (Silica Gel 230-400 mesh; 0-4percent methanol in CH2CI2 as eluent) to give 3-(4-(2-hydroxy-2-methylpropoxy)-3,5- dimethylphenyl)-6,8-dimethoxyisoquinolin-1(2H)-one (0.15 g, 46percent) as a white solid. MS (ES) m/z: 398.96 (M+1 ); MP 252-2540C

The chemical industry reduces the impact on the environment during synthesis 558-42-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
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Related Products of 23377-40-4 ,Some common heterocyclic compound, 23377-40-4, molecular formula is C19H40O2, 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.

Example 12 Ethyl 3-(hexadecyloxy)propyl {3-[({4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7- yl}methyl)amino]propyl}phosphonate (65), Scheme 12Scheme 12 (3-{[(Benzyloxy)carbonyl]amino}propyl)(ethoxy)phosphinic acid (56) (0.52 g) is evaporated twice with MeCN then dissolved in dry DCM (5 mL) and dry DMF (5 pL). This solution is then added to oxalyl chloride (574 muIota, 5 eq.) in dry DCM (5 mL) under Ar, stirred at room temperature for 2 h and then evaporated twice from dry DCM. The resulting crude phosphonyl chloride (57) in dry DCM (5 mL) is added to a solution of 3- hexadecyloxypropan-1-ol (504 mg, 1.3 eq.) and dry pyridine (1 mL) in dry DCM (3 mL). The mixture is stirred at room temperature for 3 h and then treated with saturated sodium bicarbonate solution, extracted with DCM, dried and evaporated. Flash chromatography (hexanes- EtOAc, followed by 5% v/v MeOH in EtOAc) gives benzyl N-(3-{ethoxy[3- (hexadecyloxy)propoxy]phosphoryl}propyl)carbamate (62) (110 mg). 1H NMR (500 MHz, CDCI3) delta 7.36-7.26 (m, 5H), 5.09 (s, 2H), 4.12-4.08 (m, 2H), 3.49-3.47 (m, 2H), 3.40-3.37 (m, 2H), 3.32-3.25 (m, 2H), 1.92-1.89 (m, 2H), 1.79-1.75 (m, 2H), 1.58-1.54 (m, 2H), 1.32-1.25 (m, 30H), 0.89-0.87(m, 3H). 3C NMR (125MHz, CDCI3) delta 156.4,136.6,128.5, 128.1 , 71.2, 66.6, 62.9, 61.7, 31.9, 30.9, 29.7, 29.5, 29.3, 26.2, 22.7, 16.4, 14.1. 31P NMR (202 MHz, CDCI3 ) delta 31.7. ESI-HRMS for C32H58N06PNa [M+Na]+ calcd 606.3899; found 686.3904.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.

Reference:
Patent; INDUSTRIAL RESEARCH LIMITED; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; CLINCH, Keith; CRUMP, Douglas Ronald; EVANS, Gary Brian; HAZLETON, Keith Zachary; MASON, Jennifer Mary; SCHRAMM, Vern L.; TYLER, Peter Charles; WO2012/150866; (2012); A1;,
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Application of 4541-14-4 ,Some common heterocyclic compound, 4541-14-4, molecular formula is C11H16O2, 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.

A flame-dried round-bottom flask was charged with a solution of oxalylchloride (3.8 mL, 43.1 mmol) in CH2Cl2 (45 mL) at -78 C. The mixture was added to dimethylsulfoxide (6.1 mL, 87.1 mmol) at -78 C. This mixture was stirred for 20 min,and then a solution of the alcohol (5.0 g, 27.7 mmol), prepared as described inthe preceding procedure, in CH2Cl2 (14 mL) was added.After 20 min, triethylamine (19.3 mL, 138.5 mmol) was added to the reactionmixture and stirred for 10 min. The resulting mixture was warmed to roomtemperature and stirred for 1 h. The reaction mixture was diluted with ether(30 mL), and water (30 mL) was added. The organic layer was separated, and theaqueous layer was extracted with ether (2 × 30 mL), and washed with saturatedaqueous NaHCO3 (15 mL) and saturated aqueous NaCl (15 mL). Theorganic solutions were combined, dried (Na2SO4), and concentratedto afford the desired crude aldehyde (4.90 g, 27.5 mmol, 99%) as a colorlessoil which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4541-14-4, its application will become more common.

Reference:
Article; Lee, Jungmee; Oh, Hong-Se; Kang, Han-Young; Tetrahedron Letters; vol. 56; 9; (2015); p. 1099 – 1102;,
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Adding a certain compound to certain chemical reactions, such as: 30379-58-9, Benzyl 2-hydroxyacetate, 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, SDS of cas: 30379-58-9, blongs to alcohols-buliding-blocks compound. SDS of cas: 30379-58-9

Into a 100-mL round-bottom flask, was placed (2S)-2-[[(tert- butoxy)carbonyl](methyl)amino]-3-cyclopropylpropanoic acid (1.5 g, 6.17 mmol, 1.00 equiv), benzyl 2-hydroxyacetate (1.02 g, 6.14 mmol, 1.00 equiv) in dichloromethane (30 mL). This was followed by the addition of DCC (1.52 g, 7.37 mmol, 1.20 equiv), 4-dimethylaminopyridine (900 mg, 7.37 mmol, 1.20 equiv) and HOBt (1.0 g, 7.40 mmol, 1.20 equiv) respectively in portions with stirring at 0oC. The resulting solution was stirred for 12 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (3:1). This resulted in 2 g (83%) of 2-(benzyloxy)-2- oxoethyl (2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]-3-cyclopropylpropanoate as yellow oil. MS (ES, m/z): 392 (M+H); 1HNMR (300 MHz,CDCl3, ppm): delta 7.42-7.32 (m, 5H), 5.19 (s, 2H), 4.96-4.91 (m, 0.5H), 4.71-4.65 (m, 2H), 4.65-4.63 (m, 0.5H), 2.87 (d, J=14.1 Hz, 3H), 1.90-1.62 (m, 2H), 1.47 (d, J=6.0 Hz, 9H), 0.78-0.67 (m, 1H), 0.49-0.42 (m, 2H), 0.13-0.09 (m, 2H).

The synthetic route of 30379-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERIAL, INC.; de FALLOIS, Loic, Le Hir; PACOFSKY, Gregory; LONG, Alan; MENG, Charles; LEE, Hyoung, Ik; (461 pag.)WO2017/116702; (2017); A1;,
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Reference of 37729-18-3, Adding some certain compound to certain chemical reactions, such as: 37729-18-3, name is 2-([1,1′-Biphenyl]-4-yl)ethanol,molecular formula is C14H14O, 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 37729-18-3.

2-biphenyl ethanol (1 g, 5 mmol), 4-nitrophenol (834 mg, 6 mmol), andtriphenylphosphine (1.59 g, 6 mmol) was dissolved in 20 mL dichloromethane. Thesolution was chilled in an ice-water bath prior to the addition of diethylazodicarboxylate(949 i, 6 mmol). The reaction was then stirred overnight, and the ice-water bath slowlywarmed to room temperature. Crude product was purified by flash chromatography toyield 640 mg crystalline solid. ]H NMR (400 MHz, DMSO-d6) 5 8.1 (d), 7.6 (m), 7.47-7.41 (m), 7.34 (m), 7.17 (m), 4.39 (t, 2H), 3.13 (t, 2H).

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. 37729-18-3, 2-([1,1′-Biphenyl]-4-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAECIS PHARMACEUTICALS, INC.; WO2006/20951; (2006); A1;,
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Electric Literature of 133803-81-3, Adding some certain compound to certain chemical reactions, such as: 133803-81-3, name is tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate,molecular formula is C11H22O5, 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 133803-81-3.

ferf-Butyl 3 (2 (2- hydroxyethoxy)ethoxy)propanoate (8.6 g, 37 mmol) was added to a suspension of Dess- Martin periodinane (DMP, 18.8 g, 44 mmol) and pyridine (7.0 g, 88 mmol) in DCM (150 mL) at 0C. The resulting mixture was stirred at room temperature for 16 hours, then filtered, washed with DCM (3 x 50 mL). The filtrate and washings were combined and washed with saturated NaHC03 solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography (hexane:EtOAc = 10: 1 to 3: 1) to give the title compound (4.1 g, 48%) as a yellow oil. 1H NMR (400 MHz, CDC13): delta 9.76 (s, 1H), 4.16 (s, 2H), 3.50-3.80 (m, 6H), 2.53(t, 2H), 1.46 (s, 9H).

According to the analysis of related databases, 133803-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORNELL UNIVERSITY; DANA-FARBER CANCER INSTITUTE, INC.; CHILDREN’S MEDICAL CENTER CORPORATION; MELNICK, Ari, M.; GABAS, Lorena, Fontan; US, Ilkay; CASALENA, Gabriella; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; WU, Hao; QIAO, Qi; (157 pag.)WO2018/85247; (2018); A1;,
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Related Products of 71176-54-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 71176-54-0, name is (5-Amino-1,3-phenylene)dimethanol. This compound has unique chemical properties. The synthetic route is as follows.

Compound 28:[228] To a solution of 5-nitro-m-xylene-alpha,alpha’-diol 25 (564 mg, 3.08 mmol) in methanol (35 mL) was added Pd/C (10percent, 164 mg, 0.154 mmol). Hydrogen was introduced to replace the air then the mixture was hydrogenated (H2, 5 psi) for 2 hours at room temperature. The solution was filtered through celite and the filtrate was evaporated by rotary evaporation in vacuo to give compound 26, which was dissolved in anhydrous acetonitrile (15 mL) and methyl 4- bromobutyrate (557 mg, 3.08 mmol) and potassium carbonate (426 mg, 3.08 mmol) were added. The mixture was put in a 86 0C oil bath and refluxed for 18 hours. The reaction mixture was removed from the oil bath, cooled to room temperature and diluted with dichloromethane. It was filtered through celite and the solid was washed with dichloromethane/acetonitrile (1 :1). The filtrate was evaporated under reduced pressure and the residue was purified through silica gel chromatography (Combiflash, dichloromethane/methanol) to give compound 28 (292 mg, y = 37percent) as a white solid. 1H NMR (400 MHz, MeOD): delta 6.62 (s, IH), 6.55 (s, 2H), 4.50 (s, 4H), 3.65 (s, 3H), 3.13 (d, J = 7.2 MHz, 2H), 2.43 (d, J = 7.2 MHz, 2H), 1.89 (p, J = 7.2 MHz, 2H); 13C NMR (400 MHz, MeOD): delta 175.9, 150.5, 143.7, 115.5, 111.7, 65.7, 52.2, 44.3, 32.5, 25.8; MS (m/z): found 276.0 (M + Na)+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 71176-54-0, (5-Amino-1,3-phenylene)dimethanol.

Reference:
Patent; IMMUNOGEN, INC.; LI, Wei; FISHKIN, Nathan, Elliott; ZHAO, Robert, Yongxin; MILLER, Michael, Louis; CHARI, Ravi, V., J.; WO2010/91150; (2010); 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. 1004-24-6, name is (4-Methylenecyclohexyl)methanol, the common compound, a new synthetic route is introduced below. Formula: C8H14O

To a solution of (4-methylenecyclohexyl)methanol (1.1 g, 8.72 mmol) in acetonitrile (40 mL) was added a mixture of iodine (3.32 g, 13.07 mmol) in acetonitrile (120 mL) at 0 C. The reaction mixture was stirred at 0 C for 3 h. The reaction mixture was diluted with EtOAc and washed with aq. solution of Na2S203, IN NaOH, brine, dried (MgS04) and purified on a 40 g silica gel cartridge(EtOAc/hexane: 0 to 20%) to afford the product (0.53g, 24%). 1H NMR (400MHz, CHLOROFORM-d) ppm 3.94 (s, 2H), 3.14 (s, 2H), 2.01 – 1.93 (m, 2H), 1.90 – 1.80 (m, 2H), 1.75 – 1.66 (m, 5H).

The synthetic route of 1004-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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