Tag: M.W=100-200

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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H16O4

Another exemplary study was carried out as follow: Compound J and AcOH (7.5 volumes) were charged to an appropriately sized jacketed reactor. Mixing was started and the jacket was set to maintain an internal temperature of 25 C . Tetramethoxypropane (1.01 equivalents) was charged to the reactor and the j acket was set to maintain an internal temperature of 95 C. Once at temperature, the reaction continued mixing for 1.5 hours and then an IPC sample was taken. The passing criteria for this IPC was 60 C to prevent premature precipitation. Once the target volume was reached the jacket was set to maintain an internal temperature of 50 C. A 4 M solution of NaOH was then charged to the reactor via cannula to neutralize the remaining AcOH. This typically required approximately 10 volumes of the base solution. The neutralization was monitored by pH probe. Solids began to precipitate during the course of the charge. Once neutralized, the slurry was cooled to 20 C and held at that temperature for 1 hour prior to isolation via Buchner funnel. The cake was washed twice with 2 volumes of water and once with 2 volumes of MeOH. The solids were then dried to constant weight in a vacuum oven to provide Compound H. This procedure had been performed on 110 g scale to produce a granular light brown solid.

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CRENIER, Louis; LESCARBEAU, Andre; SHARMA, Praveen; GENOV, Daniel G.; (324 pag.)WO2017/48702; (2017); A1;,
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These common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, 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. name: 1-(2-Methoxyphenyl)-N-methylmethanamine

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

The synthetic route of 1-(2-Methoxyphenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
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These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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. Formula: C9H13NO2

To a solution of (S)-2-((4-(benzyloxy)phenoxy)methyl)oxirane(1.0 g, 3.9mmol) in iPrOH (40 ml), was added 2-(2-methoxyphenoxy)ethanamine (0.98 g,5.8mmol) in iPrOH dropwise under 50C for 5h. The reaction mixture was cooled to roomtemperature, and removed the solution, water was added, extracted with EA. The organic layerwas washed with water, brine, dried over Na2SO4, concentrated under reduced pressure andpurified by silica column, to give (S)-1-(4-(benzyloxy)phenoxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol (0.52 g, 1.228mmol).

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

Reference:
Article; Yi, Bitna; Jahangir, Alam; Evans, Andrew K.; Briggs, Denise; Ravina, Kristine; Ernest, Jacqueline; Farimani, Amir B.; Sun, Wenchao; Rajadas, Jayakumar; Green, Michael; Feinberg, Evan N.; Pande, Vijay S.; Shamloo, Mehrdad; PLoS ONE; vol. 12; 7; (2017);,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: (4-(Trifluoromethoxy)phenyl)methanamine

6-((6-((4-(trifluoromethoxy)benzyl)amino)pyridazin-3-yl)oxy)quinolin-2(1H)-one To a suspension of 6-((6-chloropyridazin-3-yl)oxy)quinolin-2(1H)-one (0.032 g, 0.117 mmol) in dioxane (2.0 mL) at room temperature was added 4-(trifluoromethoxy)benzylamine (0.091 mL, 0.585 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (3.28 mg, 5.85 mumol), palladium (II) acetate (1.313 mg, 5.85 mumol) and sodium-t-butoxide (0.014 mL, 0.164 mmol). The reaction mixture was stirred in a sealed tube at 110 C. overnight, then concentrated under vacuum to a yellow oil. This was purified by prep HPLC to yield 6-((6-((4-(trifluoromethoxy)benzyl)amino)pyridazin-3-yl)oxy)quinolin-2(1H)-one as a white solid (4 mg, 5%). 1H NMR (500 MHz, METHANOL-d4) delta ppm 7.96 (d, J=9.5 Hz, 2H), 7.67-7.34 (m, 8H), 6.68 (d, J=9.6 Hz, 1H), 4.59 (s, 2H). LCMS: R.T.=1.738 min; [M+H]+=429.08.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36865-41-5, name is 1-Bromo-3-methoxypropane, belongs to ethers-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 36865-41-5, Application In Synthesis of 1-Bromo-3-methoxypropane

To a suspension of 4-chloro-3-hydroxy-5-nitrobenzamide (1.00 g, 4.62 mmol) in DMF(15 mL) was added 1-bromo-3-methoxypropane (1.06 g, 6.93 mmol) and K2C03 (1.91 mg,13.9 mmol). The reaction mixture was stirred at 60 C in a sealed tube. After 3 hr, thereaction was cooled to RT and poured into water. The resulting light yellow precipitate wascollected by filtration and washed with diethyl ether to provide the title compound (1.1 g, 3.8mmol, 83 % yield). LCMS (LCMS Method D): Rt = 0.84 mi [M+H] = 289.0

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.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHARNLEY, Adam Kenneth; DARCY, Michael Gerard; DODSON, Jason W.; DONG, Xiaoyang; FAVRE, David; HUGHES, Terry Vincent; KANG, Jianxing; LEISTER, Lara Kathryn; LI, Yuehu; LIAN, Yiqian; MEHLMANN, John F.; NEVINS, Neysa; RAMANJULU, Joshi M.; ROMANO, Joseph J.; WANG, Gren Z.; YE, Guosen; ZHANG, Daohua; (489 pag.)WO2019/69269; (2019); A1;,
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Related Products of 4344-55-2,Some common heterocyclic compound, 4344-55-2, name is 4-Butoxyaniline, molecular formula is C10H15NO, 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: Compound 51 (1.00 mmol) was suspended in dry acetonitrile (10 mL) under nitrogen atmosphere. Relevant aniline (1.00 mmol) and 4-dimethylaminopyridine (4.00 mmol) were successively added dropwise and the mixture was stirred at room temperature for 48 h. Ethyl acetate was added and the solution was washed with hydrochloric acid 1N, brine, dried over sodium sulfate, filtered, and evaporated to dryness under vacuum. The white solid was purified by flash chromatography on silica gel.

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

Reference:
Article; Fortin, Sebastien; Wei, Lianhu; Moreau, Emmanuel; Lacroix, Jacques; Cote, Marie-France; Petitclerc, Eric; Kotra, Lakshmi P.; Gaudreault, Rene C.; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5327 – 5342;,
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Some common heterocyclic compound, 461-82-5, name is 4-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, 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. Computed Properties of C7H6F3NO

4-Trifluoromethoxyaniline (1.0 g, 5.6 mmol) was dissolved in glacial acetic acid (10 mL). Bromine (585 muL, 11 mmol) dissolved in glacial acetic acid (2 mL) was added with stirring during 10 minutes at room temperature. The resulting mixture was stirred at room temperature for 2 hours and then poured into water (100 mL). The solid formed (2,5-dibromo-4-trifluoromethoxyaniline) was filtered off. The filtrate was made alkaline with solid sodium hydroxide and extracted with dichloromethane (100 mL), dried (MgSO4) and concentrated (30C; 200 mBar) to afford 0.57 g (40%) of 2-bromo-4-trifluoromethoxyaniline.1H NMR (DMSO-d6): delta 5.55 (2H, bs), 6.85 (1H, d), 7.10 (1H, dd), 7.37 (1H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 461-82-5, its application will become more common.

Reference:
Patent; NOVO NORDISK A/S; AGOURON PHARMACEUTICALS, INC.; EP1183229; (2005); B1;,
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Related Products of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 (S*)-3-methyl-7-(methylcarbamoyl)-3-phenyl-2,3-dihydrobenzofuran-5-carboxylic acid (100 mg, 0.321 mmol) in DMF (1 ml.) was added sequentially HATU (183 mg, 0.482 mmol) and DIPEA (0.140 ml_, 0.803 mmol). The reaction was stirred for 1 min then 3,3-diethoxypropan-l-amine (0.057 ml_, 0.35 mmol) was added. The reaction was stirred for 1 h. Sat. LiCI (aq) and EtOAc were added and the layers separated. The aqueous layer was extracted with further EtOAc and the organic layers were combined, back extracted with sat. LiCI (aq) and water and filtered through a cartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuo to give a dark oil. This oil was purified using silica gel column chromatography eluting with a gradient of 60-100% EtOAc : cyclohexane and the appropriate fractions collected and concentrated in vacuoto afford (S*)-N5-(3,3-diethoxypropyl)-N5′,3-dimethyl-3-phenyl-2,3-dihydrobenzofuran-5,7-dicarboxamide (141 mg, 0.320 mmol, 100 % yield) as a yellow solid LCMS (method Formic): Retention time 1.08, [M+H]” = poor ionisation

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LUCAS, Simon Christopher Cranko; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (89 pag.)WO2019/68782; (2019); A1;,
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Reference of 6298-96-0, 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Examrle 22-[(S)-1 -(4-methoxyphenyl)-ethylamino]-cyclopent-1 -ene-carboxylic acid methylester(compound of formula (IV) wherein Ar = 4-methoxyphenyl, R1 = CO2Me) 10.37 g (70.0 mmol) of 2-oxo-cyclopentane-carboxylic acid methylester (purity 96%, Aldrich) were dissolved in 30 ml of toluene and 10.00 g (65.5 mmol) of (S)-1 -(4- methoxyphenyl)-ethylamine (purity >99%, BASE) were stirred under argon for 12 hours at ca. 25C. Water was completely removed by evaporation of toluene (3 x 50 ml) andthe product was dried at 80C/i mbar to give 18.1 g (100%) of the title product asyellow oil.LC-MS: MH 276;1H NMR: 1 .40 (d, 3H, Me), 1 .65 (m, 2H, H-4), 2.25, 2.37, 2.62 (3m, 4H, H-3, H-5), 3.57(5, 3H, CO2Me), 3.73 (5, 3H, OMe), 4.60 (m, 1 H, CHN), 6,90, 7.20 (2m, 4H, Ar-H), 7.70(d, 1H, NH).

The synthetic route of 1-(4-Methoxyphenyl)ethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; KRETZSCHMAR, Gerhard; OEHME, Jan; ROSSEN, Kai; WO2015/189108; (2015); A1;,
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Electric Literature of 24599-58-4, 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. 24599-58-4, name is 2,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 1; 2,5-Dimethoxy-4-methylbenzoic acid (Compound XII); a) 2,5-Dimethoxy-4-methylbenzaldehyde; 280 ml of phosphorus oxide trichloride are admixed with 212 ml of N-methylformanilide. After 4 hours at room temperature, 110 g of 2,5-dimethoxytoluene are added and the reaction mixture is brought to 70 C. for 2 hours. The reaction mixture is poured dropwise onto ice. The precipitate obtained is filtered, taken up in dichloromethane and decanted. The organic phase is dried over anhydrous sodium sulphate and the solvents are evaporated under reduced pressure. This gives 116 g of yellow crystals; m.p.=83 C.

The chemical industry reduces the impact on the environment during synthesis 2,5-Dimethoxytoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bignon, Eric; Csikos, Eva; Frehel, Daniel; Gonczi, Csaba; Heja, Gergley; Morvai, Miklos; Podanyi, Benjamin; Schlovicsko Varkonyine, Erika; US2004/19091; (2004); A1;,
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