Tag: M.W=100-200

Application of 6850-60-8, These common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, 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 solution of 18 (75 mg, 0.25 mmol) in 5 mL EtOH in sealed tubewas added various anilines or benzylamines, the mixture was stirred at150 C. After completion, the reaction was cooled to room temperature.In the cases of solid precipitation in the reaction, the precipitates werecollected by filtration, washed with cold EtOH and dried to afford thefinal products. When no solid precipitated in the reaction, the solventwas removed in vacuo and then purified by flash column chromatographyto afford the final products.

Statistics shows that (4-Ethoxyphenyl)methanamine is playing an increasingly important role. we look forward to future research findings about 6850-60-8.

Reference:
Article; Li, Wenlong; Yin, Ying; Shuai, Wen; Xu, Feijie; Yao, Hong; Liu, Jie; Cheng, Keguang; Xu, Jinyi; Zhu, Zheying; Xu, Shengtao; Bioorganic Chemistry; vol. 83; (2019); p. 380 – 390;,
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Synthetic Route of 2186-92-7, 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. 2186-92-7, name is P-anisaldehyde dimethyl acetal belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2) Synthesis of [6-Methoxy-3,4,5-Tris(4-Methoxy-Benzyloxy)Tetrahydropyran-2-yl]Methanol of Formula (V)a) Step 1: Synthesis of 6-methoxy-2-(4-methoxyphenyl)-hexahydropyrano[3,2-D][1,3]dioxine-7,8-diol of formula (VII)The synthesis begins with the protection of the primary alcohol (VIII) (3,4,5-trihydroxy-6-methoxytetrahydro-pyran-2-ylmethanol) in the form of an acetal (VII) (6-methoxy-2-(4-methoxyphenyl)hexahydropyrano[3,2-D]-[1,3]dioxine-7,8-diol) through the action of p-anisaldehyde dimethyl acetal (III) in the presence of camphorsulfonic acid in DMF (dimethylformamide).The reaction is carried out at ambient temperature under an industrial vacuum (pressure=40 mbar) (evaporation of the methanol form) for 2 hours, so that a significant advancement in the formation of the desired product is observed, such that only traces of the starting product remain.After an aqueous treatment in a basic medium, the traces of starting product are eliminated by washing with cyclohexane; this makes it possible to isolate the compound (VII) in the form of a white solid with yields of between 60% and 80%

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, P-anisaldehyde dimethyl acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vachy, Robert; US2011/136748; (2011); 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. 121588-79-2, name is trans-4-Methoxycyclohexanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H15NO

Example 660: 2-[3-(5-chloro-2-{[trans-4-methoxycyclohexyl]amino}pyrimidin-4-yl)-5-oxo- 5H,6H,7H-pyrrolo[3,4-b]pyridin-6-yl]-N-[(1S)-2-hydroxy-1-(3-methylphenyl)ethyl]acetamide (3567) DIPEA (59.9 muIota, 0.343 mmol) was added to a stirred solution of (S)-2-(3-(2,5-dichloropyrimidin- 4-yl)-5-oxo-5H-pyrrolo[3^-b]pyridin-6(7H)-yl)-N-(2-hydroxy-1-(m-tolyl)ethyl)acetarnide (80 mg, 0.137 mmol) and (1 r,4r)-4-methoxycyclohexanamine (26.6 mg, 0.206 mmol) in dioxane (1 mL) under nitrogen. The mixture was heated to 90 C and stirred for 16 h. The mixture was allowed to cool to room temperature and was diluted with EtOAc (20 mL) and water (20 mL). The phases were separated and the aqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with brine (60 mL), dried (MgS0 ) and concentrated. The crude product was purified by chromatography (SiO2, 24 g column, 0-10% MeOH in DCM) to afford a beige solid. The product was loaded onto a column packed with SCX (0.5 g) in MeOH. The column was washed with MeOH and the product eluted with 0.7 M ammonia in MeOH. The resulting mixture was concentrated in vacuo to afford the title compound (52 mg, 66.4 %) as a beige solid. 1 H NMR (DMSO-d6, 400 MHz) delta 9.09 (1 H, s), 8.54 (1 H, d), 8.48 (1 H, s (br)), 8.40 (1 H, d), 7.62 (1 H, s (br)), 7.21 (1 H, t), 7.15 – 7.08 (2H, m), 7.07 – 7.03 (1 H, m), 4.91 (1 H, t), 4.88 – 4.80 (1 H, m), 4.64 (2H, s), 4.34 (1 H, d), 4.29 (1 H, d), 3.77 – 3.62 (1 H, m), 3.61 – 3.50 (2H, m), 3.22 (3H, s), 3.17 – 3.05 (1 H, m), 2.29 (3H, s), 2.10 – 1.84 (4H, m), 1.41 – 1.24 (2H, m), 1.24 – 1.11 (2H, m). LCMS: [M+H]+ = 565.

According to the analysis of related databases, 121588-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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Reference of 10075-63-5,Some common heterocyclic compound, 10075-63-5, name is 1,5-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

9.5 g of Intermediate 1-1 was dissolved in 150 ml of acetonitrile, and 8.9 g of N-bromosuccinimide was slowly dropwise added thereto at 0 C. for 10 minutes. The reaction mixture was slowly heated from 0 C. to ambient temperature for 4 hours, and the reaction was terminated by adding water. The reaction mixture was distilled under a reduced pressure, and the residue was subjected to extraction three times using ethyl acetate. The resultant was dried using anhydrous magnesium sulfate and distilled under a reduced pressure, and the residue was separately purified using silica gel column chromatography to obtain 12.9 g of Intermediate 1-2 (Yield: 93%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,5-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; Samsung Display Co., Ltd.; Kim, Jong Woo; Kim, Young Guk; Im, Jin Oh; Hwang, Suk Hwan; Kim, Hyung Guen; (58 pag.)KR2015/104678; (2015); A;,
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Electric Literature of 4457-67-4, A common heterocyclic compound, 4457-67-4, name is 1-Bromo-4-methoxybutane, molecular formula is C5H11BrO, 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.

(4-Methoxybutyl)(4-trifluoromethylphenyl)methanone (II) A dry three neck glass assembly, under dry nitrogen atmosphere, is charged with 150 g (6.17 moles) of magnesium and 2 L of anhydrous tetrahydrofuiran (THF). A small amount of iodine crystals or 1,2-dibromoethane is added to facilitate the initiation of Grignard reaction. The contents of the flask are heated to 75° C. and 975 g (5.84 moles) of 1-bromo-4-methoxybutane is added slowly at such a rate that the reaction maintains a spontaneous gentle reflux until the end of its addition. The Grignard reagent thus formed is cooled to 10 to 20° C. and a solution of 500 g (2.92 moles) of 4-trifluoromethylbenzonitrile in 2 L of tetrahydrofuran is introduced during a period of 1 hour to 2 hours while maintaining the reaction temperature at 16+-2° C. by external cooling, if necessary. Thereafter the temperature is raised gradually to 60 to 70° C. over a period of 1 hour and further continued at that temperature until the reaction has gone to completion. The reaction mass is cooled, then quenched into ice cold hydrochloric acid and the THF layer is separated and concentrated. The aqueous layer is further extracted with dichloromethane which is added to the concentrate of the THF layer. The resulting dichloromethane solution washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated under reduced pressure to obtain a crude product, which is further purified by high vacuum distillation. The compound (4-methoxybutyl)(4-trifluoromethylphenyl)methanone (II) is obtained in 71.84percent yield (546 g). Analytical data: m.p 40-42° C.(purified by distillation). 1H NMR: (CDCl3, 200 MHz); (delta) 1.66-1.87 (m, -(CH2)2-,4H); 3.04 (t, J=7.26 Hz, -(CH2)-, 2H); 3.33 (s, -OCH3, 3H); 3.43 (t, J=7.26 Hz, -(CH2)-, 2H); 7.72 (d, J=8.30 Hz, 2H); 8.06 (d, J=8.30 Hz, 2H).

The synthetic route of 4457-67-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Pharmaceutical Industries Ltd.; US6380436; (2002); B1;,
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Electric Literature of 40515-89-7, 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. 40515-89-7, name is Phenethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Lignin model molecule (2-phenoxy-1-phenylethanol) wassynthesized according to the method reported by Rothenberg[9]. Catalytic hydrotreating of 2-phenoxy-1-phenylethanolwas carried out in a 100ml autoclave with Tefon liner.The catalyst (50mg) was added to a solution of 2-phenoxy-1-phenylethanol (150mg) in ethanol (2ml) and H2O(8ml).The autoclave was sealed and purged with H2several times.The reaction was performed at 170C with 2MPa hydrogenpressure for 6h. Then, the reactors were cooled down toroom temperature using an ice bath, and the organic productswere extracted with ethyl acetate (5ml × 2). The organic products mixtures were analyzed by GC and chlorobenzenewas used as an external standard. Identification of mainproducts was based on GC-MS as well as by comparisonwith authentic samples. The product distribution was shownon the mole basis. In consecutive batch tests, the catalystwas recovered by magnets and washed with EtOH for threetimes. The catalyst was recycled into the autoclave with thefeedstream.

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

Reference:
Article; Chen, Bingfeng; Li, Fengbo; Yuan, Guoqing; Catalysis Letters; vol. 147; 11; (2017); p. 2877 – 2885;,
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Electric Literature of 4457-67-4, These common heterocyclic compound, 4457-67-4, name is 1-Bromo-4-methoxybutane, 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.

(2) Production of 4′-methoxybutyloxybiphenyl-4-carboxylic acid 7.2 Grams of 1-bromo-4-methoxybutane and 4.5 g of 4′-hydroxybiphenyl-4-carboxylic acid were refluxed in 100 ml of water and 400 ml of ethanol for 4 hours. Concentrated hydrochloric acid was added to the reaction mixture so that the mixture showed pH 1, then 150 ml of water was added, and the resultant mixture was refluxed for 1 hour. The reaction mixture was cooled to precipitate a crystal, and the crystal was recovered by filtration. The so-obtained crystal was recrystallized from acetone. Yield 61percent.

Statistics shows that 1-Bromo-4-methoxybutane is playing an increasingly important role. we look forward to future research findings about 4457-67-4.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; US5340498; (1994); A;,
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Reference of 2186-92-7, 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. 2186-92-7, name is P-anisaldehyde dimethyl acetal belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred benzaldehyde dimethyl acetal 1a solution of (15 mmol) was added a freshly prepared MgI2 etherate (1.5 mmol, 1.0M in Et2O/PhMe) at room temperature, followed by addition of trimethylsilyl cyanide (18 mmol). The resulting reaction mixture was stirred at room temperature for 3.0 h. chromatographic purification of the crude producton silica gel gave the 2-phenyl-2-methoxyacetonitrile 2a in 95% yield.

The synthetic route of P-anisaldehyde dimethyl acetal has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Hua; Pan, Haokun; Meng, Xiangwei; Zhang, Xingxian; Synthetic Communications; vol. 50; 5; (2020); p. 684 – 691;,
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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. 50868-72-9, name is 5-Methoxy-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H11NO

A solution of 5-methoxy-2-methylbenzenamine (1.3 g, 9.48 mmol) in 48% HBr (13 mL) and EtOH (10 mL) was cooled to 0 C. and NaNO2 (0.78 g, 11.30 mmol) in water (5 mL) was added dropwise over 15 minutes while keeping the temperature of the reaction between 0-5 C. After the clear pale brown solution was kept at 0 C. with stirring for 1 h, this solution was transferred into the boiling solution of CuBr (6.8 g, 47.4 mmol) in 48% HBr (25 mL). The solution was refluxed for overnight. The reaction mixture was cooled to room temperature and the reaction was diluted with water (50 mL). The acidic solution was extracted with ethyl acetate (2*50 mL). The combined ethyl acetate was washed by saturated NaCl (1*50 mL) and was dried over sodium sulfate. The sodium sulfate was removed by filtration and the solvent was removed by vacuum. The crude product was purified by silica gel column (3.5*16 cm) chromatography with hexanes as an eluent to yield colorless oil (750 mg, 39%).

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 50868-72-9.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
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Reference of 15799-79-8, These common heterocyclic compound, 15799-79-8, name is 3-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.

[0134] (R)-4-Oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester (Table 2, entries 11 & 12): To an amber 2-dram vial equipped with a magnetic stir bar was added (2S, 5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (6.13 mg, 0.0250 mmol, 0.100 equiv), 4-methyl ester (28.5 mg, 0.250 mmol, 1.00 equiv), CHCl3 (0.25 ml), HCl (as a 4N solution in 1,4-dioxane, 6.25 uL, 0.0250 mmol, 0.100 equiv), and 3-dimethylamino-anisole (44 uL, 0.30 mmol, 1.2 equiv). The solution was stirred for 5 min at ambient temperature and subjected directly to silica gel chromatography. Gradient elution with 20-40% EtOAc in hexanes afforded the product as a colorless oil in 73% yield (48.2 mg, 0.182 mmol); 91% ee. IR (film) 2950, 2903, 2838, 2727, 1730, 1616, 1569, 1519, 1462, 1440, 1356, 1242, 1171, 1114, 1033, 979.4, 814.6, 642.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.77 (t, J=1.1 Hz, 1H, CHO), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.27 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.22 (d, J=2.5 Hz, 1H, ArH) 4.38 (dd, J=5.2, 9.1 Hz, 1H, ArCH), 3.81 (s, 3H, ArOCH3), 3.66 (s, 3H, CO2CH3), 3.52 (ddd, J=1.4, 9.1, 18.1 Hz, 1H, CH2CO), 2.94 (s, 6H, N(CH3)2), 2.67 (ddd, J=0.8, 4.9, 17.8 Hz, 1H CH2CO); 13C NMR (75 MHz, CDCl3) ?201.0, 174.4, 157.5, 151.5, 129.3, 114.6, 104.9, 96.2, 55.6, 52.5, 46.7, 40.9, 39.2. HRMS (CI) exact mass calcd for (C21H23NO3) requires m/z 266.1392 for [M+H]+, found m/z 266.1387. [?]D=-149.0 (c=1.0, CHCl3). [0135] The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction in ethanol at 0o C.) using a Chiracel AD and AD guard column (6.0% ethanol/hexanes, 1 mL/min); S isomer tr=26.0 min, R isomer tr=27.8 min. The same reaction conducted at -20o C. on 0.5-mmol scale was complete after 8 h and purified in identical fashion to give the product in 90% yield (119 mg, 0.448 mmol) and 92% ee. EXAMPLE 8 [0104] (R)-4-Oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester (Table 1, entry 6): To an amber 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (6.13 mg, 0.0250 mmol, 0.100 equiv), CHCl3 (0.25 ml), HCl (as a 4N solution in 1,4-dioxane, 6.25 uL, 0.0250 mmol, 0.100 equiv), and 3-dimethylamino-anisole (44 uL, 0.30 mmol, 1.2 equiv). The solution was cooled to -20o C. before oxobutenoic acid methyl ester (28.5 mg, 0.250 mmol, 1.00 equiv) was added. The resulting solution was maintained at -20o C. for 8 h and then subjected directly silica gel chromatography. Gradient elution with 20-40% EtOAc in hexanes afforded the product as a colorless oil in 73% yield (48.2 mg, 0.182 mmol); 91% ee. IR (film) 2950, 2903, 2838, 2727, 1730, 1616, 1569, 1519, 1462, 1440, 1356, 1242, 1171, 1114, 1033, 979.4, 814.6, 642.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.77 (t, J=1.1 Hz, 1H, CHO), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.27 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.22 (d, J=2.5 Hz, 1H, ArH), 4.38 (dd, J=5.2, 9.1 Hz, 1H, ArCH), 3.81 (s, 3H, ArOCH3), 3.66 (s, 3H, CO2CH3), 3.52 (ddd, J=1.4, 9.1, 18.1 Hz, 1H, CH2CO), 2.94 (s, 6H, N(CH3)2), 2.67 (ddd, J=0.8, 4.9, 17.8 Hz, 1H, CH2CO); 13C NMR (75 MHz, CDCl3) ?201.0, 174.4, 157.5, 151.5, 129.3, 114.6, 104.9, 96.2, 55.6, 52.5, 46.7, 40.9, 39.2. HRMS (CI) exact mass calcd for (C21H23NO3) requires m/z 266.1392 for [M+H]+, found m/z 266.1387. [?]D=-149.0 (c=1.0, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction in ethanol at 0o C.) using a Chiracel AD and AD guard column (6.0% ethanol/hexanes, 1 mL/min); S isomer tr=26.0 min, R isomer tr=27.8 min.

The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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