Month: February 2021

Reference of 94994-15-7, These common heterocyclic compound, 94994-15-7, name is Methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, 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 solution of 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (108 mg, 0.545 mmol), methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-l-carboxylate (90 mg, 0.454 mmol) and triphenylphosphine (179 mg, 0.681 mmol) in toluene (2 mL) at 0 C was added (¡ê)-di-tert-butyl diazene-l,2-dicarboxylate (157 mg, 0.681 mmol) in toluene (0.5 mL) slowly. The reaction mixture was stirred at room temperature for 5 min and the reaction mixture was heated to 90 C for 18 hours. After cooled to room temperature, dichloromethane (5 mL) and water (5 mL) were added to the reaction mixture. The layers were separated. The organic layer was washed with brine, dried over MgS04, filtered and concentrated in vacuo to afford the crude. This crude was purified by preparative HPLC (PHENOMENEX Axia 5 muiotaeta C18 30 x 100 mm column; detection at 220 nm; flow rate = 40 mL/min; continuous gradient from 30% B to 100% B over 10 min + 5 min hold time at 100% B, where A = 90: 10:0.1 H20:MeOH:TFA and B = 90: 10:0.1 MeOH:H20:TFA) to give the title compound (75 mg, 41.5% Yield; 95% pure by LC/MS) as a light yellow oil. [M+Na]+ = 401, pi MR (400 MHz, CDC13) delta 6.70 (dd, J= 14.3, 1.6 Hz, 2H), 3.65 (s, 3H), 3.63 (s, 2H), 2.96 (s, 2H), 1.86 – 1.77 (m, 6H), 1.59 – 1.55 (m, 6H), 1.48 (s, 6H).

The synthetic route of 94994-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; ZHANG, Hao; CHENG, Peter T.W.; TAO, Shiwei; WO2014/159802; (2014); A1;,
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Some common heterocyclic compound, 175867-59-1, name is Methyl 4-aminocyclohexanecarboxylate, molecular formula is C8H15NO2, 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. COA of Formula: C8H15NO2

EXAMPLE 23(1) 2-[4-(Methoxycarbonyl)cyclohexylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (381 mg) was obtained from 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (300 mg) and methyl 4-amino-1-cyclohexanecarboxylate (222 mg) in a manner similar to Example 1(1). NMR (CDCl3, delta): 1.70-2.03 (8H, br), 2.52 (1H, br), 3.63 (1H, br), 3.71 (3H, s), 4.50 (2H, d, J=7 Hz), 5.97 (2H, s), 6.41 (1H, br), 6.66 (1H, m), 6.78-6.87 (3H, m), 8.14 (1H, m), 8.30 (1H, m), 8.86 and 9.08 (1H, br); Mass m/z: 456(M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175867-59-1, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6384080; (2002); B1;,
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Reference of 14064-10-9, These common heterocyclic compound, 14064-10-9, name is Diethyl 2-chloromalonate, 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.

4-[4-amino-5-(ethoxycarbonyl)furan-3-yl]piperazine-1-carboxylate tert-Butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate (2.35 g, crude product), diethyl chloromalonate (1.94 g, 10 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.56 g, 30 mmol) were dissolved in tetrahydrofuran (20 mL), followed by stirring at room temperature overnight. Water was added to the reaction liquid, followed by extraction with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The obtained residue was purified by using silica gel column chromatography (hexane:ethyl acetate=6:1?2:1) to give tert-butyl 4-[4-amino-5-(ethoxycarbonyl) furan-3-yl]piperazine-1-carboxylate (1.30 g, 38percent, 2 steps) as a yellow solid. 1H-NMR (CDCl3) delta: 1.38 (3H, t, J=7.1 Hz), 1.47 (9H, s), 1.87-1.95 (2H, m), 2.38-2.49 (1H, m), 2.74-2.87 (2H, m), 4.10-4.28 (2H, m), 4.35 (2H, q, J=7.1 Hz), 4.50 (2H, brs), 7.06 (1H, s).

The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOWA CO., LTD.; Morimoto, Toshiharu; Koshizawa, Tomoaki; Watanabe, Gen; Ohgiya, Tadaaki; Yamasaki, Nao; Inoue, Noriyuki; US2013/102621; (2013); A1;,
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Application of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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 solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 ¡Á 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 ¡Á 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].6-Phenylpyridin-2(1H)-one (13a)By following the general procedure, the reaction of PhCN (5a;201 mg, 1.94 mmol) with crotonate 12 (374 mg, 1.94 mmol) inthe presence of Zn (252 mg, 3.88 mmol) and TMSCl (7 mg, 3 mol%) in 1,4-dioxane (6 mL) for 4 h, followed by hydrolysis with 50%aq K2CO3 (5 mL) gave a light-yellow solid; yield: 205 mg (62%);mp 194-195 C; Rf = 0.5 (hexanes-EtOAc, 2:1).IR (KBr): 2904, 1643, 1612, 1550, 1493, 990, 921, 795, 761 cm-1.1H NMR (400 MHz, CDCl3): delta = 12.49 (br s, 1 H), 7.72 (d, J = 6.9Hz, 2 H), 7.59-7.40 (m, 4 H), 6.55-6.47 (m, 2 H). 13C NMR (100MHz, CDCl3): delta = 165.4, 147.1, 141.5, 133.6, 130.1, 129.2, 126.8,118.7, 105.0. HRMS (ESI): m/z [M + H] calcd for C11H9NO:172.0762; found: 172.0750.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rao, H. Surya Prakash; Muthanna, Nandurka; Padder, Ashiq Hussain; Synlett; vol. 29; 12; (2018); p. 1649 – 1653;,
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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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H10O3

Triphenylphosphine (538 mg, 2.05 mmol) was added to a solution of quinazolin-8-ol (250 mg, 1 .71 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (245 mg, 1 .88 mmol) was added, followed by DIAD (0.40 mL, 2.1 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 2 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-100% EtOAc: EtOH (3:1 ) in hexanes gradient to give the title compound (178 mg, 40%) as a light brown oil. 1H NMR (400 MHz, CDCI3) delta 2.65-2.75 (m, 2 H), 2.80-2.90 (m, 2 H), 3.20-3.28 (m, 1 H), 3.74 (s, 3 H), 5.10-5.15 (m, 1 H), 7.04-7.08 (m, 1 H), 7.47-7.57 (m, 2 H), 9.35-9.37 (m, 2 H); LC-MS (LC-ES) M-H = 258.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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. SDS of cas: 59247-47-1

4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester To a degassed mixture of 4-(piperazin-1-yl)-benzoic acid ethyl ester (1.45g, 6.2 mmol), 4-bromobenzoic acid tert-butyl ester (1.75g, 6.8 mmol), cesium carbonate (3.9g, 12 mmol) in dioxane (25 mL) was added tris(dibenzylideneacetone)dipalladium (300 mg, 5 molpercent) and 2-(dicyclohexylphosphino)-2′,4′,6′-tris(isopropyl)-biphenyl (x-phos, 300 mg, 10 molpercent). The mixture was heated in a sealed tube with stirring at 100 ¡ãC for 3 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The crude material was purified through a flash column chromatography using ethyl acetate and hexanes to give the intermediate 4-[4-(4-ethoxycarbonylphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester as solid (1.3 g, 51 percent yield) The above intermediate, (1.2g, 2.68 mmol) was suspended in methanol (100 mL) and THF (100 mL) and sodium hydroxide solution (1N, 80 mL) was added. The mixture was refluxed for 2 hrs and then concentrated. The mixture was acidified with 1N HCl and the solid formed was filtered to give 4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester (1.1g). LCMS calcd for C22H26N204 (m/e) 382. Obsd: 381 (M-H+)

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

Reference:
Patent; Madrigal Pharmaceuticals, Inc.; BOLIN, David, R.; CHEUNG, Adrian, Wai-hing; HAMILTON, Matthew, Michael; MARCOPULOUS, Nicholas; McDERMOTT, Lee, Apostle; QIAN, Yimin; EP2350311; (2013); B1;,
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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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 52727-57-8

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0 0C under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5- bromophenyl)methanol (1.0 g, 5.2 mmol, 59 %) as off-white solid.

According to the analysis of related databases, 52727-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITAeT SAARLANDES; WO2009/135651; (2009); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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 609-12-1, Recommanded Product: 609-12-1

To a solution (50 mL) of ethyl 3-fluoro-4-(1H-pyrazol-1-yl)phenol (2.0 g) and 2-bromo-3-methylbutanoate (2.4 mL) in dimethylformamide was added potassium carbonate (2.33 g), and the mixture was stirred at 80C for 24 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.47 g). MS (API+): [M+H]+ 307.1.

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, Ethyl 2-bromo-3-methylbutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAKAMURA, Shinji; MIKAMI, Satoshi; KAWASAKI, Masanori; NOMURA, Izumi; ASHIZAWA, Tomoko; TANIGUCHI, Takahiko; EP2873669; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, 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 50413-30-4, Quality Control of Methyl 2-amino-4-methoxylbenzoate

Methyl 2-amino-4-(methyloxy) benzoate (3.78 g, 20.86 mmol) was dissolved in 25 mL of water, 15 mL of ethanol and 2.2 mL of concentrated HCl. A solution of ICl (1.1 mL, 21.9 mmol) in 3.8 mL concentrated HCl and 14 mL of water at 5 C was added to the aniline solution. The reaction was stirred overnight and was then filtered to obtain 6.9 g of a light brown solid. MS: m/z: 308 [M+H]+

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

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; EIDAM, Patrick, M.; HAILE, Pamela, A.; MARQUIS, Robert, W., Jr.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; SINGHAUS, Robert, R., Jr.; SHAH, Ami, Lakdawala; WANG, Gren; (82 pag.)EP2744501; (2016); B1;,
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Electric Literature of 1128-00-3, A common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 solution of ethyl 2-aminocyclohex-1-enecarboxylate (33) (3.33 g, 19.7 mmol) and pyridine (2.33 g, 29.5 mmol) in dry THF (50 ml) at -5 C slowly within 1 h 2-bromoacetyl bromide (3.93 g, 19.5 mmol) was added. The reaction mixture was stirred at the same temperature for 45 min. and partitioned between ethyl acetate (50 ml) and satd NaHCO3 (50 ml). The water phase was extracted with ethyl acetate (3 ¡Á 30 ml). The organic extracts were combined, and successively washed with satd NaHCO3 solution (50 ml), water (2 ¡Á 50 ml), satd NaCl solution (50 ml), and dried (Na2SO4). The solvent was evaporated, the residue was mixed with ethyl acetate (50 ml), and the solid material was filtered off. The filtrate was evaporated to dryness and the residue was dried in vacuo over P2O5 to give 5.00 g (88%) of compound 34 as a brown oil, which was immediately utilized in the next step. 1H NMR (CDCl3) delta: 1.30 (t, J = 7.1 Hz, 3H), 1.55-1.68 (m, 4H), 2.30-2.36 (m, 2H), 2.90-2.96 (m, 2H), 3.86 (s, 2H), 4.21 (q, J = 7.1 Hz, 2H), 12.08 (br s, 1H). GCMS m/z: 289.0 M+.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
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