Category: ethers-buliding-blocks

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: 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, 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 446-59-3, Computed Properties of C7H6BrFO

To a solution of the above compound (58mg, 0. 224MMOL) in CH, CI (LML) cooled over dry ice/acetone bath was added boron TRIBROMIDE (224UL, 0. 224MMOL) and stirred over night at room temperature. After this time, the mixture was treated with methanol (3X5ML) and concentrated in vacuo to give 2-(1,1-dioxido-1, 2-thiazinan-2-yl) -3-fluorophenol. Low resolution mass spectrometry: (M+H+)= 246.16. 1H NMR (400MHZ, CDC13) 8 7.19 (dd, 1H, J=8.4 and 15HZ), 6.81 (d, 1H, J=8.4Hz), 6.70 (t, 1H, lOHz), 3.82-3. 90 (M, 1H), 3.60-3. 68 (m, 1H), 3.34-3. 43 (M, 1H), 3.26-3. 34 (M, 1H), 2.34-2. 43 (m, 2H), 1.94-2. 08 (M, 1H) and 1.77-1. 89 (M, 1H) ppm.

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, 2-Bromo-1-fluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2005/16886; (2005); 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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Adding a certain compound to certain chemical reactions, such as: 106854-77-7, name is 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene, 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 106854-77-7, Computed Properties of C8H6BrF3O

EXAMPLE 7 4-(2,2,2-Trifluoroethoxy)phenylhydrazine hydrochloride A solution of 4-bromophenyl 2,2,2-trifluoroethyl ether (5.2 g, 20 mmol) in THF (75 ml) was cooled to -75 C. under nitrogen. A solution of 2.7M n-butyllithium (7.5 ml, 20 mmol) was added dropwise. After 15 minutes, a solution of di-t-butylazodicarboxylate (4.5 g, 19 mmol) in THF (30 ml) was added quickly with stirring. The solution was allowed to warm to -40 C., resulting in the formation of a precipitate. Acetic acid (1.5 ml), water (10 ml), saturated sodium chloride (10 ml) and hexane (100 ml) were then added to the mixture. The organic solution was dried over MgSO4, filtered and evaporated. The residue was dissolved in 1:1 carbon tetrachloride-hexane and left to crystallize overnight. The resulting crystalline precipitate was collected, providing 4.25 g of white powder.

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, 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ortho Pharmaceutical Corporation; US4864032; (1989); A;,
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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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Application of 332-48-9, 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 116 1-(2-(4-Fluorophenoxy)ethyl)-4-(4-methylbenzyl)piperidine hydrochloride STR152 From a mixture of 4-(4-methylbenzyl)piperidine (500 mg, 2.21 mmol), 2-(4-fluorophenoxy)ethyl bromide (508 mg, 2.32 mmol) and K2 CO3 (626 mg, 4.53 mmol) in CH3 CN (20 mL) was obtained the title compound as colorless plates (293 mg, 63%), mp 189-191 C., 1 H NMR (CDCl3) 1.60-2.12 (m, 5H), 2.31 (s, 3H), 2.57 (d, J=7.2 Hz, 2H), 2.62-2.82 (m, 2H), 3.20-3.55 (m, 2H), 3.65 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-6.84 (m, 2H), 6.92-7.02 (m, 6H), 7.08 (d, J=8.1 Hz, 2H), 12.56 (bs, 1H); Anal. Calcd for C21 H27 ClFNO: C, 69.31; H, 7.48; N, 3.85. Found: C, 69.49; H, 7.39; N, 3.88.

The synthetic route of 1-(2-Bromoethoxy)-4-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
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