Tag: M.W=100-200

The chemical industry reduces the impact on the environment during synthesis 366-99-4, name is 3-Fluoro-4-methoxyaniline, I believe this compound will play a more active role in future production and life. 366-99-4

Cyanuric chloride (1.84 g, 10 mmol) inCH3CN (20 mL) was cooled toabout-10 C was added3-fluoro-p-anisidine (1. 41 g, 10 mmol) followed by DIEA(1. 8 mL, 10 mmol). The reaction was stirred for about 45 min then at room temperature for about 45 min under an N2 atmosphere. Cycloheptylamine (1.26 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the reaction was stirred at room temperature overnight.N,N-dimethylethylenediamine (1. 1 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the mixture was heated at reflux under N2 overnight. The reaction was diluted with ethyl acetate, washed with brine, and dried over anhydrousK2C03. The material (1.178 g) was purified by silica gel column chromatography to afford a solid 150 (1.178 g,28percent), mp73-76 C ; HPLC: Inertsil ODS-3VC18, 40: 30: 30[KH2PO4 (O. 01M, pH 3.2) :CH30H :CH3CN], 264 nm,Rt 10.8 min, 95. 1percent purity ; MS (ESI):iiilz418 (M+H, 100), 373(11. 9), 322 (7.8), 277 (6.8), 162 (3.6).

The chemical industry reduces the impact on the environment during synthesis 366-99-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 51; 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-difluoromethoxy-phenyl)-amide; To a solution of 4-(6,7-dimethoxy-quinazolin-4-yl)-piperidine-1-carbonyl chloride (46.9 mg, 0.14 mmol), as prepared in Example 3a, in DMSO (1 mL) was added 4-(difluoromethoxy)aniline (26.6 mg, 0.17 mmol), followed by DIEA (35.9 mg, 0.28 mmol). The mixture was heated at 100 C. with stirring. After 2 h, it was cooled to room temperature and partitioned between EtOAc and water. The combined EtOAc extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc?5% MeOH/EtOAc as eluent) to afford the title compound as a white solid (20.4 mg, 32%). 1H NMR (300 MHz, CDCl3) delta 9.09 (s, 1H), 7.40 (s, 1H), 7.38 (d, J=8.99 Hz, 2H), 7.27 (s, 1H), 7.07 (d, J=8.93 Hz, 2H), 6.48 (s, 1H), 6.45 (t, J=74.22 Hz, 1H), 4.28 (m, 2H), 4.08 (s, 3H), 4.07 (s, 3H), 3.62 (m, 1H), 3.20 (td, J=13.02 and 2.64 Hz, 2H), 2.14 (m, 2H), 2.01 (m, 2H). LC-MS (ESI) calcd mass 458.2, found 459.3 (MH+).

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; Baindur, Nand; Gaul, Michael David; Kreutter, Kevin Douglas; Baumann, Christian Andrew; Kim, Alexander J.; Xu, Guozhang; Tuman, Robert W.; Johnson, Dana L.; US2006/281772; (2006); A1;,
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A common compound: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 702-24-9

A solution of amine (68 mg, 0.45 mmol) and IBX (252 mg, 0.90 mmol) in 10 mL of CHCl3 was heated at reflux with vigorous stirring for 6 h. The suspension was filtered and the filtrate was washed in sequence with 10percent NaOH (5 mL x 3), 1 M HCl (5 mL x 3), and water. The organic layer was dried with MgSO4 and concentrated in vacuo to afford the desired product (57 mg, 91percent yield). 1H NMR (400 MHz, 25 ¡ãC, CDCl3): delta = 9.89 (s, 1H), 7.85 (d, 2H, J = 8.0 Hz), 7.01 (d, 2H, J = 8.0 Hz), 3.90 (s, 3H) ppm. 13C NMR (100 MHz, 25 ¡ãC, CDCl3): delta = 190.89, 164.60, 132.01, 129.91, 114.31, 55.60 ppm. ESI?MS: M + Na+, found 159.1 (calc. 159.15).

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, 702-24-9, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Li-Xia; Huang, Yin-Hui; Cong, Hang; Tao, Zhu; Chemical Papers; vol. 72; 3; (2018); p. 661 – 667;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 929-75-9 name is 1,11-Diamino-3,6,9-trioxaundecane, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 929-75-9

The compound 2-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)-2-oxo-piperazin-1-yl)acetic acid (25mg, 0.017mmol), HATU (14.45mg, 0.038mmol), DIPEA (6.1mg, 0.05mmol) was dissolved in dry DMF, the1,11-diamino-3,6,9-trioxaundecane (3.3 mg, 0.017 mmol) was slowly added dropwise to the above solution, and after reacting at room temperature for 1 h,The reaction was detected to be complete. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (eluent, dichloromethane / methanol = 100/3).18 mg of a pale yellow solid was obtained with a yield of 64.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,11-Diamino-3,6,9-trioxaundecane, and friends who are interested can also refer to it.

Reference:
Patent; Second Military Medical University; Sheng Chunquan; Dong Guoqiang; Ma Junhui; He Shipeng; Fang Yuxin; Wu Shanchao; Chen Shuqiang; (19 pag.)CN110563706; (2019); A;,
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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 54149-17-6 as follows. 54149-17-6

Under an argon atmosphere, bisimine 11 (3.0 g, 10.12 mmol, 1 eq.), 1-bromo-2-(2-methoxyethoxy) ethane (3.35 mL, 22.26 mmol, 2.2 eq.) of and K2CO3 (5.59 g, 40.48 mmol, 4 eq.) were dissolved in 150 mL of dry DMF in a vacuum dried Schlenk flask. The contents were heated at 100C for 24 hours and the reaction was cooled to room temperature and 200 mL of distilled water was added to it. This was then extracted with EtOAc (3¡Á200 mL) and washed with distilled water (300 mL) and with brine (200 mL). The organic layers were combined and dried over anhydrous Na2SO4 and concentrated in vacuuo to yield a brownish-yellow coloured paste. This paste was thoroughly washed with pentane (3¡Á20 mL) and dried to a yellow powder.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shahane, Saurabh; Toupet, Loic; Fischmeister, Cedric; Bruneau, Christian; European Journal of Inorganic Chemistry; 1; (2013); p. 54 – 60;,
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A common compound: 115144-40-6, name is 3,4-Difluoroanisole, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 115144-40-6

a) 7.29 ml (66.3 mmol) of titanium tetrachloride were added while stirring to a solution, cooled to 0, of 5.73 g (39.8 mmol) of 3,4-difluoroanisole in 30 ml of anhydrous dichloromethane. Subsequently, the mixture was treated dropwise over 10 minutes with 3.51 ml (39.6 mmol) of 1,1-dichloromethyl methyl ketone and stirred at room temperature for one hour. The mixture was poured into 100 ml of ice-water, extracted twice with 150 ml of dichloromethane each time and the combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution. After drying over magnesium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1). There were obtained 5.8 g (84%) of 4,5-difluoro-2-methoxybenzaldehyde as a white solid with m.p. 74.

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, 115144-40-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US5955495; (1999); A;,
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The chemical industry reduces the impact on the environment during synthesis 1535-73-5, name is 3-Trifluoromethoxyaniline, I believe this compound will play a more active role in future production and life. 1535-73-5

Example 61 : 6-(6-Amino-pyrimidin-4-ylsulfanyl)-naphthalene-1-carboxylic acid (3- trifluoromethoxy-phenvP-amide; To 95 mg (0.32 mMol) 6-(amino-pyrimidin-4-ylsulfanyl)-naphthalene-1-carboxylic acid, 85 mg(0.48 mMol) 3-trifluoromethoxy-aniline, 446 mul (3.2 mMol) Et3N and 4 mg (0.03 mMol) DMAP EPO in 3 ml DMF, 0.37 ml (0.63 mMol) propylphosphonic anhydride are added. After 3 h at rt, the reaction mixture is worked up as described for Ex. 58, yielding the title compound: m.p.: 197- 199 ¡ãC; MS: [M+1]+ = 457.

The chemical industry reduces the impact on the environment during synthesis 1535-73-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/59234; (2006); A2;,
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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 111-95-5 as follows. 111-95-5

Bis(2-methoxyethyl)amine (9.0 mL, 60.8 mmol, 1.8 eq.) was added dropwise to a solutionof PCl3 (3.0 mL, 34.3 mmol) in dry hexane (90 mL) under N2 at 0 C. The resulting white slurrywas stirred at 20 C for 1 h, filtered and washed with hexanes (3x 100 mL). The solvent wasremoved (rotavap) and the residue distilled under reduced pressure (125 C, 100 mmHg). Theproduct was isolated as a colorless clear liquid (5.14 g, 64%).Data for 29a:1H-NMR: (500 MHz, CDCl3)delta 3.33 (s, 6 H, OCH3), 3.49 (s, 8 H, 1-H, 2-H).13C-NMR: (125 MHz, CDCl3)delta 48.6 (d, J = 16.8 Hz), 58.9, 71.1 (d, J = 2.6 Hz).31P NMR: (200 MHz, CDCl3)delta -84.2.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Boese, Dietrich; Denmark, Scott E.; Synlett; vol. 29; 4; (2018); p. 433 – 439;,
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349-65-5, A common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

Synthesis of N-(2-Methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) Urea To a solution of 2-methoxy-5-(trifluoromethyl)aniline (0.15 g) in anh CH2Cl2 (15 mL) at 0 C. was added CDI (0.13 g). The resulting solution was allowed to warm to room temp. over 1 h, was stirred at room temp. for 16 h, then was treated with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (0.18 g). The resulting yellow solution was stirred at room temp. for 72 h, then was treated with H2O (125 mL). The resulting aqueous mixture was extracted with EtOAc (2*150 mL). The combined organics were washed with a saturated NaCl solution (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated (90% EtOAc/10% hexane). The resulting white solids were collected by filtration and washed with EtOAc. The filtrate was concentrated under reduced pressure and the residual oil purified by column chromatography (gradient from 33% EtOAc/67% hexane to 50% EtOAc/50% hexane to 100% EtOAc) to give N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea as a light tan solid (0.098 g, 30%): TLC (100% EtOAc) Rf 0.62; 1H NMR (DMSO-d6) delta2.76 (d, J=4.8 Hz, 3H), 3.96 (s, 3H), 7.1-7.6 and 8.4-8.6 (m, 11H), 8.75 (d, J=4.8 Hz, 1H), 9.55 (s, 1H); FAB-MS m/z 461 ((M+H)+).

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); 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. 4179-19-5, name is 3,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows., 4179-19-5

1,3-dimethoxy-5-methylbenzene (30 g, 0.20 mol) and dichloromethane (900 mL) were added to a dry round bottom flask (1 L).To the above solution, a sulfone dichloride (52.5 g, 0.40 mol) was added dropwise under ice-cooling, and the mixture was stirred and stirred at room temperature overnight.After the reaction was completed, NaHCO3 aqueous solution was added dropwise to adjust pH=8, extracted with dichloromethane, washed with dilute hydrochloric acid and distilled water, and dried.Concentration under reduced pressure gave the compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene (31 g, white solid).

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; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wang Hui; (20 pag.)CN110016026; (2019); A;,
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