Author: Jessica.F

Synthetic Route of 701-56-4, These common heterocyclic compound, 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, 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: To a screw-capped tube (5 mL) containing freshly distilled MeCN (2.0-3.0 mL) was successively added CoCl2 (0.10 equiv for N-substituted maleimide), an aromatic tertiary amine (2.0 equiv for N-substituted maleimide), an N-substituted maleimide (0.50-1.0 mmol), and 5.5 M TBHP in decane solution (1.5 equiv for N-substituted maleimide) under N2 atmosphere. After the tube was sealed with a cap that contained a PTFE septum, the resultant mixture was stirred at 60 C (bath temperature). After cooling to room temperature, the mixture was passed through a silica gel-packed short column (EtOAc as the eluent), and the filtrate was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane : EtOAc =5 : 1) to give the corresponding tetrahydroquinoline derivative. If necessary, the isolated product was further purified by a preparative HPLC equipped with a GPC column (chloroform as the eluent).

The synthetic route of 701-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakai, Norio; Matsumoto, Shun; Ogiwara, Yohei; Tetrahedron Letters; vol. 57; 49; (2016); p. 5449 – 5452;,
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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. 136-90-3, name is 4-Methoxy-3-methylphenylamine, A new synthetic method of this compound is introduced below., SDS of cas: 136-90-3

Compound 107 3-[[(3S)-tetrahydrofuran-3-yl]sulfamoyl]benzoic acid (270 mg, 1.0 mmol) was dissolved in dichloromethane (5 mL). 3-methyl-4-methoxyaniline (165 mg, 1.2 mmol) and triethylamine (145 mg, 1.4 mmol) were added to the mixture at 20C. The mixture was stirred at 20C for 5 minutes. HATU (456 mg, 1.2 mol) was added and the mixture was further stirred at 20C for 8 hours. The solvent was removed in vacuo and the obtained residue was purified by high performance liquid chromatography (Column: Phenomenex Synergi C18 150*20mm*5um.. A: H2O+0.1%TFA B: MeCN from 30% to 60 % B in A). The product fractions were collected and the organic solvent was evaporated in vacuo. The aqueous layer was neutralized with saturated aqueous NaHCC>3 and extracted with dichloromethane (2 x 10 mL). The combine organic layers was dried over Na2S04 and concentrated in vacuo resulting in compound 107 (135 mg). Method A; Rt: 5.24 min. m/z : 391.3 (M+H)+ Exact mass: 390.1

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; JANSSEN R&D IRELAND; LAST, Stefaan, Julien; RABOISSON, Pierre, Jean-Marie, Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; WO2014/33176; (2014); A1;,
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Reference of 658-89-9, The chemical industry reduces the impact on the environment during synthesis 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

Intermediate 51 : Mixture of (trans)-N-{2-amino-4-[(trifluoromethyl)oxy1phenyl)-3-(6-methyl- 2-pyridinyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8-carboxamide and (trans)-N-{2-amino-5- [(trifluoromethyl)oxy1phenyl)-3-(6-methyl-2-pyridinyl)-2-oxo-1-oxa-3-azaspiro[4.51decane- 8-carboxamide; To a shaken mixture of (trans)-3-(6-methyl-2-pyridinyl)-2-oxo-1-oxa-3- azaspiro[4.5]decane-8-carboxylic acid (Intermediate 52, 65.4 mg, 0.225 mmol) and 4- [(trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 64.9 mg, 0.338 mmol) in pyridine (1.5 ml) was added EDCHCI (86 mg, 0.451 mmol) and the mixture was shaken for 2 hours. The mixture was concentrated under vacuum; the residue was partitioned between saturated sodium bicarbonate solution and EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under vacuum to give a residue. The residue was purified twice by silica gel chromatography (elution in gradient with 0-100% Et2ODCM) to afford the title compound as brown residue (98 mg, 80%). No further purification followed. UPLC-MS: 0.76 min, m/z 465 [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, 4-(Trifluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
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5397-31-9, name is 3-((2-Ethylhexyl)oxy)propan-1-amine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-((2-Ethylhexyl)oxy)propan-1-amine

Example 13A reaction vessel was charged with 180 parts by weight of 3-(2-ethylhexyloxy)propylamine, 180 parts by weight of DL-4,4-dimethyl pyroglutamine acid, and 100 parts by weight of methanol, and the mixture was stirred at 70 C. for 3 hours. The resulting reaction mixture was stripped at 90 C. under reduced pressure to remove the methanol, and 335 parts by weight of white solid was obtained at a yield of 93%. Results of the 13C-NMR shown in Table 13, below, and absorption at 1685 cm-1 (from amide bond) in the measurement of IR spectrum confirmed that the resulting product was an amino acid compound represented by the following formula: TABLE 13 13C-NMR (CDCl3) 11.2~74.3ppm (CH, -CH2-, -CH3) 180.9ppm (-NH-CO-) 35.0ppm (-CO-C) 22.4ppm (C-CH3) 41.8ppm (-C-CH2-) 56.4ppm [-CH(NH2)(COOH)] 179.2ppm (-COOH)

The synthetic route of 5397-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MORIYA, Hiroyuki; US2011/144369; (2011); A1;,
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Synthetic Route of 207226-31-1, These common heterocyclic compound, 207226-31-1, name is 1,3-Dibromo-5-(trifluoromethoxy)benzene, 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.

EXAMPLE 57 6-(3-Bromo-5-trifluoromethoxy-Phenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]-oxazin-2-one Prepared from (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1,3-dibromo-5-trifluoromethoxybenzene according to Procedure B. White solid: mp 214-216 C.; 1H-NMR (DMSO-d6) delta10.4 (s, 1H), 7.99 (s, 1H), 7.73 (s, 1H), 7.68-7.62 (m, 3H), 6.97 (d, 1H, J=8.0 Hz), 1.68 (s, 6H); MS (ESI) m/z 414 ([M’H]-, 100%); Anal. Calc. For C17H13BrF3NO3: C, 49.06, H, 3.15, N, 3.37. Found: C, 49.16, H, 3.05, N, 3.30.

The synthetic route of 207226-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6444668; (2002); B1;,
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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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromo-2-(trifluoromethoxy)aniline

240 g (0.937 mol) of 5-bromo-2-(trifluoromethoxy)aniline were dissolved in 2400 mL of anh toluene. 112 mL (1.406 mol) of chloroacetyl chloride were added. It was stirred for 2 h at 100 C. The reaction mixture was concentrated on the rotavap. The residue was treated with 600 mL of cyclopentyl methyl ether and concentrated again. This procedure was performed twice yielding 324 g of the title compound. 1H-NM (400MHz, DMSO-d6): delta [ppm]= 4.39 (s, 2H), 7.40 – 7.44 (m, 1H), 7.49 (dd, 1H), 8.20 (d, 1H), 10.23 (s, 1H). LC-MS (Method 4): Rt = 1.27 min; MS (ESIpos): m/z = 332 [M+H]+.

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William J.; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; GEISLER, Jens; WO2015/140196; (2015); 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11BrO

General procedure: To a stirred solution of 1-(2-pyridyl)-b-carboline (0.245 g,1 mmol) in 10 mL DMF, sodium hydride (50% in mineral oil, 0.048 g,1 mmol) and bromo-hydrocarbon (1 mmol) was added. The reactionmixturewas stirred at room temperature for 1 h. After reactionwas finished, the mixture was poured into ice water and extractedwith ethyl acetate. The organic layer was washed with water anddried. Removal of the solvent gave the crude product that waspurified by silica gel column (dichloromethane: methanol 100:1 as the eluent). The solvent was removed and the product wasobtained.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1462-37-9.

Reference:
Article; Lu, Xing; Liu, Yan-Cheng; Orvig; Liang, Hong; Chen, Zhen-Feng; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Product Details of 5905-69-1

Step 4) 1-difluoromethoxy-4-{3-[3-(2-fluoro-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-Fluoro-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (349 mg, 0.973 mmol) was dissolved in THF (2 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (2 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (300 mg 1.30 mmol), copper iodide (35 mg, 0.131 mmol), tetrakis(triphenylphosphine)palladium (70 mg, 0.060 mmol) and triethylamine (4.3 g, 42.5 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%, then 5% EtOAc in hexanes) afforded an oil 178 mg (53%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.68-1.80 (m, 2H) 1.85-2.11 (m, 2H) 2.17-2.36 (m, 2H) 2.38-2.43 (m, 1H) 3.28-3.65 (m, 1H) 4.24-4.52 (m, 2H) 7.01-7.47 (m, 5H) 7.18 (d, J=8.8 Hz, 2H) 7.58 (d, J=8.8 Hz, 2H).

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; WYETH; US2009/48320; (2009); A1;,
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Synthetic Route of 22094-18-4, These common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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.

Intermediate 314A: 1-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile To a suspension of NaH (0.733 g, 18.32 mmol, 60% in mineral oil) in DMF (14 mL) was added 2-(4-bromophenyl)acetonitrile (1.796 g, 9.16 mmol) followed by 1,3-dibromo-2,2-dimethoxypropane (2.0 g, 7.64 mmol) and the reaction mixture was heated to 60 C. and stirred for 12 h. The reaction mixture was cooled to RT, poured into water (150 mL) and extracted with EtOAc (3*40 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (24 g REDISEP column, eluting with 5% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 314A as a white solid (2 g, 88%). 1H NMR (300 MHz, DMSO-d6) delta ppm 7.68-7.57 (m, 2H), 7.46-7.40 (m, 2H), 3.18 (s, 3H), 3.08 (s, 1H), 3.07 (s, 3H), 3.05-3.02 (m, 1H), 2.74-2.71 (m, 1H), 2.70-2.67 (m, 1H).

Statistics shows that 1,3-Dibromo-2,2-dimethoxypropane is playing an increasingly important role. we look forward to future research findings about 22094-18-4.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Adding a certain compound to certain chemical reactions, such as: 645-36-3, name is 2,2-Diethoxyethanamine, 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 645-36-3, Computed Properties of C6H15NO2

N-(3-Bromo-4-chlorobenzyl)-2,2-diethoxyethanamine To a solution of 3-bromo-4-chlorobenzaldehyde (10.0 g, 45 mmol) and 2,2-diethoxyethanamine (6.68 g,50 mmol) in 200 mL of DCM at RT, 0.5 mL of AcOH was added and the resulting mixture was stirred at RT for 30 min. To this mixture, NaCNBH3 (8.1 g, 135 mmol) was added in portions and then stirred at RT overnight. The reaction mixture was portioned between water and DCM. The organic layer was washed with water (80 mL x 2) and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the desired product (11 g, 72% yield) as an oil. The crude product obtained was used directly in the next step without further purification

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

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; WU, Tao; REN, Pingda; LIU, Yi; LIU, Yuan; LONG, Yun, Oliver; WO2015/54572; (2015); A1;,
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