Month: June 2021

Reference of 69812-51-7, These common heterocyclic compound, 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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.

To a stirred solution of 5-amino-l,3-dihydro-2H-benzo[d]imidazol-2-one50 (50 mg) in pyridine (0.5 ml) was added methyl 4-(chlorosulfonyl)benzoate 163 (78.7 mg). The reaction mixture was stirred at room temperature for 1 h. LC-MS analysis indicated that the reaction was complete. The reaction mixture was poured into EtOAc/THF (1 :3) and extracted sequentially with diluted 2 M aq. HCl and with saturated brine. The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was taken up in dichloromethane and the mixture was ultrasonicated at room temperature. The mixture was then filtered through sintered glass, and the solid was dried in vacuo to afford methyl 4-(N-(2-oxo-2,3-dihydro-lH-benzo[d]imidazol-5- yl)sulfamoyl)benzoate (101 mg, 87 %) as an off-white solid. MS (ISP): 348.1 ([M+H]+).

Statistics shows that Methyl 4-chlorosulfonylbenzoate is playing an increasingly important role. we look forward to future research findings about 69812-51-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 50893-36-2, name is 1-Chloroethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Chloroethyl ethyl carbonate

EXAMPLE 16 1-[(Ethoxycarbonyl)oxy]ethyl 2-[3-(2-thienyl)acrylamido]benzoate A mixture of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) and triethylamine (0.2 ml, 1.4 mmol) in dry acetone (10 ml) was stirred at room temperature for 30 minutes. To the solution, 1-chloroethyl ethyl carbonate (214 mg, 1.4 mmol) and sodium iodide (210 mg, 1.4 mmol) were added under ice cooling, and the mixture was heated under reflux for 19 hours. The reaction mixture was filtered by suction and the solvent was removed from the filtrate. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate, then with saturated aqueous sodium chloride, and dried over magnesium sulfate. After removing the solvent, the residue was purified by silica gel column chromatography (developing solvent:benzene:ether=49:1). The second elude was collected. After removing the solvent, the resulted oily product was crystallized with isopropyl ether to give the desired compound (98 mg, yield, 25percent). m.p., 154°-156° C. (white crystals, recrystallized from methanol/tetrahydrofuran/water). IR (KBr, cm-1): 3250, 1755, 1690 (shoulder), 1670 1 H-NMR (CDCl3, delta): 1.32 (t, 3H, –CH2 CH3), 1.67 (d, 3H, –CH(CH3)–), 4.23 (q, 2H, –CH2 CH3), 6.17-8.17 (m, 9H, aromatic hydrogen, vinyl hydrogen, –CH(CH3)–), 8.83 (d, 1H, aromatic hydrogen), 11.13 (brs, 1H, –CONH–)

The synthetic route of 50893-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sawai Pharmaceutical Co., Ltd.; US5006548; (1991); A;,
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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. 4897-84-1, name is Methyl 4-bromobutanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4897-84-1

A mixture of vanillin (20.0 g, 131 mmol), methyl 4-bromobutanoate (17.5 mL, 139 mmol) and potassium carbonate (27.2 g, 197 mmol) in A V-dimethylformamide (100 mL) was stirred at room temperature for 18 h. The reaction mixture was diluted with water (500 mL) and the title compound (30.2 g, 91%) was obtained by filtration as a white solid. The product was carried through to the next step without any further purification. (1374) NMR (400 MHz, CDCI3) delta 9.84 (s, lH), 7-46-7-37 (m, 2H), 6.98 (d, J=8.2 Hz, lH), 4.16 (t, J=6.3 Hz, 2H), 3.91 (s, 3H), 3.69 (s, 3H), 2.56 (t, J=7.2 Hz, 2H), 2.20 (quin, J=6.7 Hz, 2H); FontWeight=”Bold” FontSize=”10″ C NMR (100 MHz, CDC13) delta 190.9, 173.4, 153-8, 149-9, 130-1, 126.8, 111.6, 109.2, 67.8, 56.0, 51.7, 30.3, 24.2; MS M/Z (EIMS) = 271.9 (M+Na)+, 253 (M+H)+; LCMS (Method A): tR = 6.48 min.

The synthetic route of 4897-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FEMTOGENIX LIMITED; JACKSON, Paul Joseph Mark; THURSTON, David Edwin; RAHMAN, Khondaker Mirazur; (243 pag.)WO2017/194960; (2017); 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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H11NO2

To a solution of the benzyl amine (179 mg, 1.08 mmol) and DIPEA (0.45 ml, 2.6 mmol) in CH2Cl2 (5 ml) was carefully added triphosgene (150 mg, 0.51 mmol) and the resulting solution was stirred at room temperature for 20 minutes (Majer, P.; Randad, R.S. J Org. Chem., 1994, 59, 1937-1938). A solution of 4-[(thiophen-3-ylmethyl)-amino]-piperidine- 1-carboxylic acid tert-huty ester (455 mg, 1.53 mmol) in CH2Cl2 (2 ml) was then added and the reaction was stirred at room temperature for an additional 18 hours. The mixture was diluted with saturated aqueous NaHCO3 (25 ml) and was extracted with CH2Cl2 (20 ml X 3). The combined organic solution was washed with brine (50 ml), was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/Et2O, 9:1, increased to 3:1) gave the urea as a light yellow foam (236 mg, 45%). 1H NMR (CDCl3) delta 1.43 (s, 9H), 1.44-1.58 (m, 2H), 1.69-1.79 (m, 2H), 2.71-2.85 (m, 2H), 3.89 (s, 3H), 4.09-4.24 (m, 2H), 4.33 (s, 2H), 4.39 (d, 2H, J= 5.8 Hz), 4.54 (tt, IH, J= 12.0, 3.7 Hz), 4.80 (t, IH, J= 5.7 Hz), 6.95 (d, IH, J= 4.8 Hz), 7.07 (d, IH, J- 1.5 Hz), 7.13 (d, 2H, J= 8.5 Hz), 7.34 (dd, IH, J= 5.0, 2.9 Hz), 7.91 (d, 2H, J- 8.5 Hz).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANORMED INC.; WO2006/138350; (2006); A2;,
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Related Products of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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 of tert-butyl 4-((2-(2-(3-(tert-butoxy)-3- oxopropoxy)ethoxy)ethyl)amino)piperidine- 1-carboxylate (211)[00554] To a dried scintillation vial containing a magnetic stir bar was added tert-butyl 4-oxopiperidine-1-carboxylate (399 mg, 2 mmol), H2N-PEG2-COOt-Bu (550 mg, 2.4 mmol), 4 A molecular sieves (activated powder, 200 mg), and 1,2-dichloroethane (5 mL). The mixture was stirred for 1 h at room temperature. To the reaction mixture was added sodium triacetoxyborohydride (845 mg, 4 mmol). The mixture was stirred for 3 days at room temperature. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 850 mg of compound 211 as a viscous oil. [00555] MS (ESI) mlz: [M+H]Calcd for C21H41N206 417.3; Found 417.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 9-Amino-4,7-dioxanonanoate, its application will become more common.

Reference:
Patent; REDWOOD BIOSCIENCE, INC.; RABUKA, David; ALBERS, Aaron Edward; BARFIELD, Robyn M.; DEHART, Gregory W.; DRAKE, Penelope M.; KUDIRKA, Romas Alvydas; GAROFALO, Albert W.; McFARLAND, Jesse M.; WO2015/187428; (2015); A1;,
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Application of 89-91-8, These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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 dimethoxyacetate (19.9 g, 148 mmol) and compound C2 (15.6 g, 74.2 mmol) were combined with molecular sieves (16 g), and the mixture was treated with a solution of potassium t-butoxide in THF (1.0M, 150 mL, 150 mmol). The reaction mixture was heated to reflux for about 18 h; it was then filtered, and the collected solid was rinsed with additional THF. The combined filtrates were neutralized with acetic acid and concentrated in vacuo. The residue was purified by silica gel chromatography (Eluant: 5% MeOH in chloroform) to afford C10 as a white solid. Yield: 9.8 g, 33 mmol, 44%. MS (APCI) m/z 295.2 (M+1). 1H NMR (300 MHz, CDCl3) delta 1.91 (br d, J=10.5 Hz, 2H), 2.38 (m, 2H), 3.48 (s, 6H), 3.60 (dd, J=11, 12, 2H), 4.14 (br d, J=11 Hz, 2H), 4.90 (m, 1H), 5.22 (s, 1H), 8.10 (s, 1H), 9.52 (br s, 1H).

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2010/190771; (2010); 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.

A mixture of di-tert-butyl malonate (4.3 g, 19.91 mmol, 1.99 equiv) and potassium carbonate (2.8 g, 20.29 mmol, 2.03 equiv) in N,N-dimethylformamide (30 mL) was stirred at 65 C. for 30 min A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (2.65 g, 10.00 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) was then added dropwise with stiffing to the reaction mixture. The resulting solution was stirred at 65 C. overnight and then quenched with 60 mL of ice and water. The mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 3×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 4.0 g (90%) of methyl 4-(4-(3-tert-butoxy-2-(tert-butoxycarbonyl)-3-oxopropyl)-5-methyloxazol-2-yl)benzoate as a light yellow solid. LC-MS: (ES, m/z): 446 [M+H]+, 390, 334, 272, 230, 115.

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; The Board of Trustees of the Leland Stanford Junior University; Auckland UniServices Limited; Ruga Corporation; Giaccia, Amato; Lai, Edwin; Razorenova, Olga; Chan, Denise; Hay, Michael Patrick; Bonnet, Muriel; Sun, Connie; Tabibiazar, Ray; Yuen, Po-wai; US2015/329503; (2015); A1;,
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Application of 15441-07-3, The chemical industry reduces the impact on the environment during synthesis 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, I believe this compound will play a more active role in future production and life.

d Methyl 3-[2-(2-phenylthioethoxy)ethylaminosulphonyl]propanoate The subtitle compound (2.85 g) was prepared according to the procedure in example 5 part d using 2-(2-phenylthioethoxy)ethanamine hydrochloride (6 g), triethylamine (4 ml) methyl 3-(chlorosulphonyl)propanoate (5.8 g), and dichloromethane (50 ml). Mass spectrum FAB 348 (M+105).

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-(chlorosulfonyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Astra Pharmaceuticals Limited; US5846989; (1998); A;,
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Electric Literature of 31600-43-8, 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 31600-43-8 as follows.

[00459] Methyl 2-(benzyloxy)acetate (112) (5.5 g, 30.6 mmol) was dissolved in THF (30 mL). LiAlD4 (1.4 g, 35 mmol) was added at 0 C and the reaction mixture was stirred for 3 h. Water (1.4 mL) was added to quench the reaction. 10% aqueous NaOH solution (2.8 mL) and water (4.2 mL) were added. The mixture was filtered through a pad of CELITE, and the precipitate was washed with THF. The filtrate was dried over anhydrous Na2S04, and concentrated to give crude product, which was purified by silica gel chromatography (30% EtO Ac/petroleum ether) to obtain 2-(benzyloxy)-l,l-dideuteroethanol (113) Yield (3.4 g, 74%). LCMS: m/z 177.1 [M+Na]+; tR = 1.40 min.

According to the analysis of related databases, 31600-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; MCCAULEY, Dilara; LANDESMAN, Yosef; GOLAN, Gali; KALID, Ori; SHECHTER, Sharon; WO2015/42414; (2015); A1;,
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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 152849-72-4 as follows. category: esters-buliding-blocks

A mixture of methyl 5-bromo-2,4-dimethyl-benzoate (400 mg, 1.65 mmol), LiOH (197 mg, 8.21 mmol) in tetrahydrofuran (3 mL) and water (3 mL) was stirred under N2 at 70 C. for 3 h. The reaction was then diluted with 30 mL of water and 20 mL of EtOAc. The mixture was then adjusted pH to 4-5 with 1N HCl. The organic layer was concentrated to dryness to give the title compound as a white solid (350 mg, 92.9% yield). LCMS (ESI) [M+H]+=230.9.

According to the analysis of related databases, 152849-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
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