Month: March 2021

Electric Literature of 26583-60-8, 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 26583-60-8 as follows.

EXAMPLE 12 2-{4-[2-Hydroxy-3-(2-(2-methyl-phenoxy)-ethylamino)-propoxy]-phenyl}-3-methyl-8-methoxy-3,4-dihydro-quinazolin-4-one This compound was prepared analogous to Example 2 from 2-[4-(1,2-epoxy-propoxy)-phenyl]-3-methyl-8-methoxy-3,4-dihydro-quinazolin-4-one and 2-(2-methyl-phenoxy)-ethylamine. M.p. of the hydrochloride: 120-125 C. Yield: 45% of theory. C28 H32 ClN3 O5 (526.04): Calc.: C-63.93%; H-6.13%; N-7.99%; Cl-6.73%. Found: C-63.81%; H-6.04%; N-8.03%; Cl-6.84%.

According to the analysis of related databases, 26583-60-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4379788; (1983); A;,
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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. 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Fluoro-2-isopropoxyaniline

To a solution of ethyl 7-methylsulfanylthiazolo[5,4-d]pyrimidine-2-carboxylate (O.5g, 1 ,9mmol) in DCM (20m1) was added m-CPBA (675mg, 3.9mmol) and stirred for 2 hours at room temperature. 4-Fluoro-2-isopropxyaniline (331 mg, I .9mmol) in dioxane (20ml)was then added and stirred for 1.5 hours. The mixture was diluted with DCM and water, the organic layer separated, dried and concentrated onto silica. The compound was purified via column chromatography (20-80%EtOAc in Pet. Ether) to give an orange solid (706mg, 95%); 1H NMR (400 MHz, CHLOROFORM-d) O ppm 1.45 (d, J=5.95 Hz, 6 H), 1.50 (t, J=6.90 Hz, 3 H), 4.52 – 4.58 (m, 2 H), 4.58 – 4.67 (m, I H), 6.69 – 6.81 (m,2 H), 8.55 (dd, J=8.93, 6.18 Hz1 I H), 8.68 (a, 1 H), 8.69 – 8.73 (m, I H); LC-MS (ESI):(MHj 377.1

According to the analysis of related databases, 148583-65-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; WINTER-HOLT, Jon James; MCIVER, Edward Giles; AMBLER, Martin; LEWIS, Stephen; OSBORNE, Joanne; WEBB-SMITH, Kayleigh; (257 pag.)WO2017/85484; (2017); A1;,
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Synthetic Route of 16728-64-6, A common heterocyclic compound, 16728-64-6, name is 3-(Benzyloxy)propan-1-amine, molecular formula is C10H15NO, 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.

(c) In an analogous manner to that described in Example 133 (b), from 3-benzyloxy-propylamine and tert-butyl (3RS,4RS)-4-(2-methylsulphonyl-pyrimidin-5-yl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate [Example 129 (c)] there was obtained tert-butyl (3RS,4RS)-4-[2-(3-benzyloxy-propylamino)-pyrimidin-5-yl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate in the form of a brownish gum; MS: 583 (M+H)+.

The synthetic route of 16728-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US6051712; (2000); A;,
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Related Products of 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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.

A suspension of l-methyl-5-(2-phenyl-[l,2,4]triazolo[l,5-a]pyridin-7-ylcarbamoyl)-lH- pyrazole-4-carboxylic acid with 1 eq. lithium chloride (80 mg, 0.198 mmol), bis(2- methoxyethyl) amine (87 ul, 0.59 mmole), diisopropylethylamine (104 ul, 0.59 mmol) and propylphosphonic anhydride (50 % in ethyl acetate, 291 ul, 0.494 mmol) in tetrahydrofurane (4 ml) is stirred for 2.5 hours at 70 C giving after 20 min a light yellow solution. The cooled solution is diluted with ethyl acetate, washed once with sat. aqueous sodium carbonate solution, once with IN aqueous hydrochloric acid, once with brine, dried with magnesium sulfate and the solvent is evaporated to dryness affording N4,N4-bis(2-methoxyethyl)-l-methyl-N5-(2-phenyl- [l,2,4]triazolo[l,5-a]pyridin-7-yl)-lH-pyrazole-4,5-dicarboxamide (80 mg, 84.8%) as a colorless waxy solid. MS: m/z= 478.2 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(2-methoxyethyl)amine, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; PETERS, Jens-Uwe; WO2012/76430; (2012); A1;,
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Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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. category: ethers-buliding-blocks

To a cooled solution of methyl 3-chloro-4-{[(2,4-dimethoxybenzyl)(l,3-thiazol-2- yl)amino]sulfonyl}benzoate (Preparation 7, lOOmg, 0.21mmol, leq) and Et3N (44muL, 0.32mmol, 1.5eq) in THF (6ml) was added l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (106mg, 0.55mmol, 1.3eq) and 1-hydroxybenzotriazole (58mg, 0.43mmol, leq). The reaction mixture was stirred at 00C for 20 minutes before the addition of 4- (trifluoromethoxy)benzylamine (36muL, 0.23mmol, l.leq) and then stirred for a further 18 hours. The solvent was evaporated in vacuo and the residue partitioned between DCM (15ml) and water (15ml) then passed through a phase separation cartridge. The organic phase was concentrated and the residue redissolved in 4.5M HCl in 1,4-dioxane (5ml) and the solution stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue purified by preparative HPLC to yield the title compound.[0355] LCMS Rt= 3.27 min. MS m/z 491.99 [MH]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93919-56-3, its application will become more common.

Reference:
Patent; ICAGEN, INC.; PFIZER LIMITED; WO2008/118758; (2008); A1;,
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Related Products of 52189-63-6, These common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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.

28.22 g of 3,5-dimethoxy-5-fluorobenzene was weighed into a 1,000 mE round bottom flask fitted with a stir bar, reflux condenser, nitrogen inlet, and cap. A nitrogen atmosphere was established and maintained throughout the reaction. 200 mE of anhydrous CC14 was added, followed by 32.61 g of N-bromosuccinimide (NI3S). The remaining NI3S powder residue was washed into the flask with 100 mE of CC14. The reaction mixture was stirred at reflux under N, for 4 h, during which time the suspended yellow solids changed color to white. At completion, the precipitated succinimide solids were filtered off and washed thoroughly with 200 mE heptane. The CC14 was removed from the filtrate by rotary evaporation at 50 C. More succinimide precipitated from the heptane solution and was removed by filtration while the solution was still warm. The remaining heptane was removed in vacuo to obtain a clear, amber oil (40.67 g), which solidified on standing. Purification of the crude material was accomplished by distillation. The condenser was kept at 50 C. to prevent the product from solidi1zing before reaching the collection flask. After a small impurity fraction was collected at 78 C./8 torr, the product distilled at 123-125 C./8 ton. The clear pale yellow liquid solidified to an off-white solid on standing (37.88

The synthetic route of 52189-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HINMAN, Andrew W.; Davis, Dana; Kheifets, Viktoria; US2014/256830; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 30568-44-6, name is 2-(4-Methoxyphenyl)propan-2-amine, 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 30568-44-6, HPLC of Formula: C10H15NO

General procedure: (3S,4S)-4-{[4-(1H-Benzimidazol-2-yl)piperazin-1-yl]carbonyl}-3-(thiophen-3-yl)cyclohexanone (30 mg, 0.07 mmol) was dissolved in a mixture of MeOH (367 muL) and DCE (367 muL), and 2-(4-methoxyphenyl)propan-2-amine (59.2 mg, 0.29 mmol) was added followed by MP-cyanoborohydride (159 mg, 0.367 mmol) and acetic acid (13.0 muL, 0.22 mmol) at rt. The reaction mixture was shaken overnight at 55 C, cooled to rt, filtered and concentrated under vacuum. LC-MS indicated a 3:2 ratio of diastereomeric reductive amination products.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Methoxyphenyl)propan-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Anthony Romero; Hastings, Nicholas B.; Moningka, Remond; Guo, Zhiqiang; Wang, Ming; Di Salvo, Jerry; Lei, Ying; Trusca, Dorina; Deng, Qiaolin; Tong, Vincent; Terebetski, Jenna L.; Ball, Richard G.; Ujjainwalla, Feroze; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1014 – 1018;,
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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. 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: ethers-buliding-blocks

General procedure: A pyrex test tube containing solid of 1,3,5-trimethoxybenzene (1a, 0.3 mmol), carbon tetrabromide (0.075 mmol), AQN-2-CO2H (0.03 mmol) and dry EtOH (5 mL) was irradiated for 20 h at roomtemperature with stirring by a 21W fluorescent lamp under air. The reactionmixture was concentrated in vacuo, quenched with aq Na2S2O3 and extractedwith EtOAc. The organic layer was dried over MgSO4 and concentrated invacuo. Purification of the residue by flash chromatography on silica gel(hexane/ethyl acetate = 6:1) provided 2-bromo-1,3,5-trimethoxybenzene (2a)(66.8 mg, 90%,) as a white solid.

The synthetic route of 6443-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanaka, Masanori; Kamito, Yuji; Lei, Cui; Tada, Norihiro; Itoh, Akichika; Tetrahedron Letters; vol. 56; 43; (2015); p. 5886 – 5888;,
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Electric Literature of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)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.

Methyl 2-oxindoline-6-carboxylate (20 g, 105 mmol) was charged to the reaction vessel. The vessel was equipped with thermometer, stirrer and condenser. Toluene (100 ml, 5 vol) was added followed by acetic anhydride (90 ml, 954 mmol) and the mixture was heated to reflux (115-118 C ). Reflux was continued for 18 hours and a sample was analyzed by HPLC for methyl 2-oxindoline-6-carboxylate (nmt 2.0 a-%). When the methyl 2-oxindoline-6-carboxylate was consumed 40 ml (2 vol) of solvent was distilled off followed by addition of fresh toluene (40 ml, 2 vol). Trimethyl orthobenzoate (53.9 ml, 314 mmol) was added to the boiling reaction during a couple of minutes maintaining the temperature above 110 C . After the addition was complete distillation began and the temperature of the reaction mixture was above 120 C. Eight volumes (160 ml) of solvents were distilled of after which the reaction temperature was adjusted between 110-115 C. The reflux was continued for two hours and precipitation of methyl (E)-l -acetyl-3 -(methoxy(phenyl)methylene)-2- oxoindoline-6-carboxylate began during the reaction. According to HPLC- chromatogram 93.6 % conversion was achieved. The reaction mixture was allowed to cool to room temperature during 5 hours, and then further cooled to 0 C and stirred for two hours at 0 C. The precipitate was filtered and washed with EtOAc (2 x 20 ml, 2 x 1 vol) and dried in vacuum oven at 60 C for 16 hours to obtain the product (33.99 g, 90.85 %, 98.36 a-%) as tan powder. H NMR (400 MHz, DMSO- d6): delta 8.89 (dd, J= 1.5 Hz, J= 0.6 Hz, 1H), 8.0 (dd, J= 8.0 Hz, J= 1.6 Hz, 1H), 7.94 (dd, J= 8.1 Hz, J= 1.6 Hz, 1H), 7.69-7.53 (m, 3H), 7.48-7.33 (m, 2H), 3.93 (s, 3H), 3.76 (s, 3H), 2.57 (s, 3H).13C NMR (l00 MHz, DMSO-d6 ): delta 171.6, 171.3, 167.3, 167.2, 136.8, 131.0, 130.9, 129.1, 128.8, 128.5, 128.1, 126.5, 122.6, 116.7, 106.3, 57.9, 52.2, 27.0.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERMION OY; PIISOLA, Antti; TOIS, Jan; (13 pag.)WO2019/97112; (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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Formula: C13H13NO

General procedure: A mixture of 5 (1 eq.) and amine (2 eq.) in ethanol was stirred at 85 C for 3 h. The mixture was concentrated and purified by flash column chromatography to give compound 6.

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:
Article; Park, Sun Jun; Kim, Eunjin; Yoo, Miyoun; Lee, Joo-Youn; Park, Chi Hoon; Hwang, Jong Yeon; Ha, Jae Du; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4399 – 4404;,
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