Author: tianli

Reference of 517-21-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 517-21-5, name is Sodium 1,2-dihydroxyethane-1,2-disulfonate, molecular formula is C2H4Na2O8S2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 4Preparation of Compound Vareniclina (I)[0079]A solution prepared dissolving a compound of formula (IV) (30.0 g, 0.12 mols) in 440 mL of tetrahydrofuran is loaded in a 1 L flask.[0080]33 g of Pd/C (containing 58.5% w/w of water, 3.97 mmols of Pd, 3% molar) are added, maintaining the reaction mixture under stirring. The reaction environment is saturated with hydrogen at atmospheric pressure and left to react for 48 h at room temperature. The suspension is filtered on celite and the panel is first washed with tetrahydrofuran and then with water. The collected organic phases are directly transferred in a 2 L flask, whereas the aqueous phase is first treated with the glyoxal sodium bisulphite adduct (VI) (34.3 g, 0.13 mols) and then added to the organic phase. The so obtained biphasic mixture is heated at 55 C. and maintained under strong stirring for two hours. The phases are separated and the organic one is concentrated under reduced pressure. The obtained residue is added to the aqueous phase previously removed. The aqueous mixture is treated with a solution of 30% NaOH till it is actually basic. The product is extracted more times with dichloromethane and the organic phases are collected and dried with anhydrous sodium sulphate, filtered off and the solvent is removed by distillation under reduced pressure. Solid Varenicline (I) (20.5 g) is obtained with a yield of 70% in two steps starting from the compound of formula (IV).

According to the analysis of related databases, 517-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIPHARMA FRANCIS S.r.l.; ATTOLINO, Emanuele; ROSSI, Roberto; ALLEGRINI, Pietro; US2013/30179; (2013); A1;,
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Electric Literature of 623-50-7, 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.623-50-7, name is Ethyl 2-hydroxyacetate, molecular formula is C4H8O3, molecular weight is 104.1045, as common compound, the synthetic route is as follows.

Step A: Ethyl 3-(2-ethoxy-2-oxoethoxy)isonicotinate: Triphenylphosphine (150.6 g, 574 mmol) was dissolved in THF (1 L) and cooled to -10 C. To this was added DIAD dropwise via an addition funnel over 30 minutes. The resulting white suspension was kept at -10 C. for another 30 minutes. Ethyl glycolate (50.84 mL, 526.4 mmol) was added as a solution in THF (500 mL) via the addition funnel at a rate to maintain the internal temperature below -10 C. Upon completion of addition, the reaction mixture was kept at -10 C. for additional 30 minutes before a suspension of ethyl 3-hydroxyisonicotinate (80 g, 478.6 mmol) in THF (500 mL) was added. The reaction was allowed to warm up slowly to ambient temperature overnight. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate (1 L) and extracted with 1N HCl. The aqueous layer was treated with NaHCO3 to pH 8 and then extracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated to give the desired product (92.0 g, 76%). MS (APCI) m/z 254.3 (M+1).

The chemical industry reduces the impact on the environment during synthesis 623-50-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
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Synthetic Route of 2807-30-9 , The common heterocyclic compound, 2807-30-9, name is 2-Propoxyethanol, molecular formula is C5H12O2, 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.

General procedure: A mixture of the corresponding 4-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-6-aryl-3,4,5,6-tetrahydropyrido[2,3-d]pyrimidine-7(8H)-one (14{x}) (0.42mmol), Cs2CO3 (0.54mmol) and the corresponding alcohol (9mL) was heated a reflux overnight. The resulting solution was cooled down, water (100mL) was added and the reaction crude was neutralized with 2M HCl. The resulting solid was collected by filtration and washed with water, and EtOEt to afford the corresponding 15{x,y}. Starting from compound 14{5} and 2-propoxyethanol to afford 15{5,9} in 38% yield, white solid. IR (KBr), numax (cm-1): 3479, 3332, 3220, 2773, 1692, 1631, 1575, 1458, 1435, 1373, 777. 1H NMR (400 MHz, DMSO-d6): delta 10.51 (s, 1H, NH), 7.58-7.47 (m, 2H, C13-CH), 7.37 (t, J = 8.1 Hz, 1H, C14-CH), 6.42 (s, 2H, NH2), 4.63 (dd, J = 12.9, 9.2 Hz, 1H, C7-CH), 4.35-4.32 (m, 2H, C15-CH2), 3.63 (t, J = 4.9 Hz, 2H, C16-CH2), 3.35 (t, J = 6.6 Hz, 2H, C17-CH2), 2.93-2.79 (m, 2H, C6-CH2), 1.46 (h, J = 7.3 Hz, 2H, C18-CH2), 0.80 (t, J = 7.4 Hz, 3H, CH3). 13C NMR (100.6 MHz, DMSO-d6): delta 169.6, 166.4, 161.8, 158.0, 135.3, 135.1, 129.8, 128.3, 85.2 (C5), 71.9 (C17), 68.2 (C16), 65.0 (C15), 43.1 (C7), 22.4 (C18), 22.2 (C16), 10.4 (C19). Anal. Calcd. (%) for C18H20Cl2N4O2: C, 52.57; H, 4.90; N, 13.62. Found: C, 52.76; H, 5.12; N, 13.98.

The synthetic route of 2807-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Camarasa, Marta; De La Bellacasa, Raimon Puig; Gonzalez, Alex L.; Ondono, Rauel; Estrada, Roger; Franco, Sandra; Badia, Roger; Este, Jose; Martinez, Miguel Angel; Teixido, Jordi; Clotet, Bonaventura; Borrell, Jose I.; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 463 – 483;,
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Reference of 575-03-1, Adding some certain compound to certain chemical reactions, such as: 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin,molecular formula is C10H5F3O3, 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 575-03-1.

General procedure: The appropriate bromoketone (6a-o) (1.7 mmol) and triethylamine (1.6 mmol) were added to as olution of either7-hydroxy-4-methyl-2H-chromen-2-one 4 (1.4 mmol)or 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one 5 (1.4 mmol) in THF (20 mL). The mixture was stirred at room temperature for 24h, filtered and the solvent was evaporated under reduced pressure.The solid residue was purified by column chromatography eluting with DCM/MeOH 9:1 to afford (7a-n) and (8a-o).

According to the analysis of related databases, 575-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kandil, Sahar; Westwell, Andrew D.; Mcguigan, Christopher; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2000 – 2004;,
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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 597-31-9, name is 3-Hydroxy-2,2-dimethylpropanal. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H10O2

Example 214 3-(((3R,3aS,9bS)-9b-((4-fluorophenyl)sulfonyl)-7-(perfluoropropan-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-yl)amino)-2,2-dimethylpropan-1-ol A solution of (3R,3aS,9bS)-9b-((4-fluorophenyl)sulfonyl)-7-(perfluoropropan-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-amine (Example 114; 20.0 mg, 0.039 mmol) in DCM (1 mL) was treated with DIEA (14 muL, 0.078 mmol) and 3-hydroxy-2,2-dimethylpropanal (39.8 mg, 0.390 mmol) and stirred at rt. After 45 min the mixture was treated with sodium triacetoxyborohydride (33.0 mg, 0.156 mmol) and stirred at rt overnight. The mixture was treated with a drop of saturated aqueous NaHCO3, concentrated and purified by preparative HPLC (Method E, gradient 48-88% B, 20 min) to provide 3-(((3R,3aS,9bS)-9b-((4-fluorophenyl)sulfonyl)-7-(perfluoropropan-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-yl)amino)-2,2-dimethylpropan-1-ol (7.2 mg, 30% yield). LCMS m/z 600.2 (M+H)+; HPLC tR 1.91 min (Method C). 1H NMR (500 MHz, DMSO-d6) delta 7.48 (s, 2H), 7.36-7.20 (m, 5H), 3.25-3.14 (m, 2H), 2.98 (br dd, J=10.8, 3.5 Hz, 1H), 2.82 (q, J=7.2 Hz, 1H), 2.73-2.66 (m, 1H), 2.61 (br d, J=15.6 Hz, 1H), 2.48-2.32 (m, 2H), 2.22-2.06 (m, 2H), 2.03-1.82 (m, 3H), 1.75-1.60 (m, 1H), 1.35-1.17 (m, 1H), 0.82 (2s, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 597-31-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Marcoux, David; Beaudoin Bertrand, Myra; Dhar, T.G. Murali; Yang, Michael G.; Xiao, Zili; Xiao, Hai-Yun; Zhu, Yeheng; Weigelt, Carolyn A.; Batt, Douglas G; (154 pag.)US2018/127368; (2018); A1;,
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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. 1211539-82-0, name is 2,2-Difluorobenzo[d][1,3]dioxol-5-ol. This compound has unique chemical properties. The synthetic route is as follows. name: 2,2-Difluorobenzo[d][1,3]dioxol-5-ol

To a solution of Example 29A (3.0 g, 17.23 mmol) in N,N-dimethylformamide (30 mL) at ambient temperature was added potassium carbonate (4.76 g, 34.5 mmol) and tert-butyl bromoacetate (2.91 mL, 19.82 mmol). This mixture was warmed to 65 C and was allowed to stir for 1.5 hours. The mixture was allowed to cool to ambient temperature and was then partitioned between ethyl acetate (50 mL) and H2O (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 × 15 mL). The combined organic fractions were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 5.5 g of tert-butyl 2-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)oxy)acetate, which was used without further purification. To a mixture of tert-butyl 2-((2,2- difluorobenzo[d][1,3]dioxol-5-yl)oxy)acetate (5.0 g, 17.35 mmol) in methanol (60 mL) and water (20.00 mL) was added NaOH (17.35 mL, 87 mmol, 5 M aqueous solution). This mixture was allowed to stir at ambient temperature for 2 hours, and then it was concentrated under reduced pressure. The residue was dissolved in water, and the pH was adjusted to ~1 with 1 N HCl. The resulting solid was collected by filtration to give the title compound (3.28 g, 14.13 mmol, 81% yield) as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1211539-82-0, 2,2-Difluorobenzo[d][1,3]dioxol-5-ol.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 16700-55-3, (2,6-Dimethoxyphenyl)methanol, 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, Quality Control of (2,6-Dimethoxyphenyl)methanol, blongs to alcohols-buliding-blocks compound. Quality Control of (2,6-Dimethoxyphenyl)methanol

Step A Synthesis of 2,6-dimethoxyphenylmethyl bromide as an intermediate After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction.

The synthetic route of 16700-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5569664; (1996); A;; ; Patent; FMC Corporation; US5639763; (1997); A;,
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Adding a certain compound to certain chemical reactions, such as: 4249-72-3, 2-Phenoxy-1-phenylethanol, 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, Formula: C14H14O2, blongs to alcohols-buliding-blocks compound. Formula: C14H14O2

2-phenoxy-1-phenylethan-1-ol ((50 gm, 0.236 mmol), TEMPO (7.3 mg, 0.047 mmol), CuCl (4.6 mg, 0.047 mmol), NMI (7.7 mg, 0.94 mmol), bpy (7.3 mg, 0.047 mmol) and MeCN (.93 mL, 0.25 M of substrate) stirred under an air atmosphere (1 atm) at 25 C for 20 h. The reaction mixture was quenched with 1 N HCl and product were extracted with dichloromethane. The organic layer was washed with the water, dried over MgSO4 and concentrated under vacuum. The products were separated by silica-gel column chromatography (EtOAc:hexane 1:20) to produce 2-phenoxy-1-phenylethan-1-ol (48 mg, 0.224 mmol, 95%), 2-phenoxy-1-phenylethan-1-one (2.5 mg, 0.012 mmol, 5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4249-72-3, 2-Phenoxy-1-phenylethanol, and friends who are interested can also refer to it.

Reference:
Article; Patil, Nikhil D.; Yan, Ning; Tetrahedron Letters; vol. 57; 27-28; (2016); p. 3024 – 3028;,
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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 162744-59-4, name is (4-Bromo-2,6-difluorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. name: (4-Bromo-2,6-difluorophenyl)methanol

To a mixture of 4-bromo-2,6-difluorobenzyl alcohol (1.00 g, 4.48 mmol) in DCM (20 mL) is added Dess-Martin periodinane (2.12 g, 5.00 mmol). This mixture is stirred 2 h at RT. The mixture is then partitioned between EtOAc and sat. aq. NaHC03. The organic phase is washed with brine, dried over MgS04, filtered and concentrated. The crude product is purified by flash chromatography to afford aldehyde 14a1.

With the rapid development of chemical substances, we look forward to future research findings about 162744-59-4.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; STAMMERS, Timothy; BARBEAU, Xavier; BEAULIEU, Pierre; BERTRAND-LAPERLE, Megan; BROCHU, Christian; EDWARDS, Paul, J.; FORGIONE, Pasquale; GODBOUT, Cedrickx; HUCKE, Oliver; JOLY, Marc-Andre; LANDRY, Serge; LEPAGE, Olivier; NAUD, Julie; PESANT, Marc; POIRIER, Martin; POIRIER, Maude; THAVONEKHAM, Bounkham; WO2011/32277; (2011); 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. 3068-00-6, name is 1,2,4-Butanetriol, the common compound, a new synthetic route is introduced below. Product Details of 3068-00-6

A 100 mL RBF was charged with dilinolenyl ketone (Compound 7) (4.2 g, 8.2 mmol), 1,2,4-butanetriol (3.4 g, 32 mmol), PPTS (200 mg, 0.8 mmol) and a stir bar. The flask was flushed with nitrogen and anhydrous toluene (60 mL) added. The reaction vessel was fitted with a Dean Stark tube and condenser and brought to reflux and the reaction was left overnight. After cooling to room temperature, the reaction mixture diluted with toluene (50 mL), and washed with 5% aq. Na2C03 (2 chi 50 mL), water (50 mL), dried (MgS04) and purified by chromatography to yield 3.0 g (4.9 mmol, 59%) of the ketal.

The synthetic route of 3068-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTIVA BIOTHERAPEUTICS, INC; HEYES, James; WOOD, Mark; MARTIN, Alan; WO2011/141704; (2011); A1;,
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