Month: September 2021

74137-36-3, The chemical industry reduces the impact on the environment during synthesis 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, I believe this compound will play a more active role in future production and life.

Tris(dibenzylideneacetone)dipalladium(0) (6.53 g, 7.15 mmol) was added in one portion to a stirred solution of the bromide of Preparation 1 (38.0 g, 143 mmol), 1,1′-bis(diphenylphosphino)ferrocene (9.3 g, 16.8 mmol) and zinc cyanide (20.0 g, 172 mmol) in N,N-dimethylformamide (300 ml) at room temperature under nitrogen. The reaction was heated at 100° C. for 14 hours and cooled to room temperature. Water (1500 ml) was added and the mixture was extracted with ethyl acetate (3.x.500 ml). The combined organics were filtered and the filtrate was washed with water (500 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene (1000 ml) to provide the title compound (18.0 g) as a tan solid. 1H-NMR (300 MHz, CDCl3): delta=3.83 (3H, s), 7.31 (2H, s), 7.48 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US2005/54707; (2005); A1;,
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Electric Literature of 6851-80-5, The chemical industry reduces the impact on the environment during synthesis 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

a N-(2-Methoxybenzyl)–N-(methyl)aminoacetonitrile A mixture of 2.0 g (13.2 mmole) of N-methyl-2methoxybenzylamine, 0.99 g (13.2 mmole) of chloroacetonitrile, and 2.80 g (26.5 mmole) of powdered sodium carbonate was stirred in 30 mL of acetone at room temperature for 4 days. The mixture was concentrated in vacuo and the residue purified by flash chromatography on 130 g of silica gel eluding with 83:17 hexanes: ethyl acetate to give 2.2g (87%) of an oil. 1 H NMR (CDCl3, 400 MHz, ppm): delta 2.43 (s, 3H), 3.48 (s, 2H), 3.62 (s, 2H), 3.83 (s, 3H), 6.88 (d, 1H), 6.93 (t, 1H), 7.2-7.3 (m, 2H).

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-(2-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5610165; (1997); A;,
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Application of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: The orthoester (1.5 equiv) was added to a mixture of the 3-amino-2,2-dimethylpropionamide(1.0 equiv) in anhydrous ethanol (3 mL). Glacial acetic acid (2 equiv) was added and the reactionwas heated at reflux for 24 h. The reaction mixture was cooled and concentrated under vacuum.The product was hygroscopic and was best crystallized by adding purified chloroform and allowing itto sit under nitrogen for 4?7 days. Filtration and drying yielded the pure product.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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Electric Literature of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 26; 5-Chloro-thiophene-2-carboxylic acid (2,2-diethoxyethyl) amide; Add 5-chlorothiophene-2-carboxylic acid (100 g, 0.60 mol) and dichloromethane (1000 mL) to a 3 L three-necked round bottom flask equipped with an overhead stirrer, nitrogen inlet/outlet, addition funnel, and thermocouple. Stir the resulting solution under nitrogen while cooling to 4 0C. Add via addition funnel 2,2-diethyoxyethylamine (88.5 ml, 0.60 mol) in dichloromethane (35 mL) over 12 minutes. Add l-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (123 g, 0.64 mol) to the chilled mixture. Add additional dichloromethane (165 mL) and stir the reaction mixture for 22 h at room temperature. Quench the reaction with water (1000 mL) and separate the resulting layers. Back extract the aqueous layer with dichloromethane (500 mL) and combine the organic layers. Dry over sodium sulfate and purify through a silica gel bed eluting with dichloromethane followed by a mixture of 1% MeOH in dichloromethane and then a mixture of 10% MeOH in dichloromethane to afford 108 g (65%) of the title compound as a white solid. 1H NMR (500 MHz, CDCl3): delta 7.26 (d, J= 3.5 Hz, IH), 6.85 (d, J= 3.5 Hz, IH), 6.37 (bs, IH), 4.57 (t, J= 5.5 Hz, IH), 3.68-3.74 (m, 2H), 3.48-3.57 (m, 4H), 1.19 (t, J= 7.5 Hz, 6H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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Reference of 1017779-69-9, A common heterocyclic compound, 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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 14 N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0292) To a mixture of 3-fluoro-4-(trifluoromethoxy)aniline (66 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (63 mg). 1H NMR (300 MHz, CDCl3) delta3.98 (2H, s), 6.82 (1H, d, J = 6.8 Hz), 7.08-7.24 (3H, m), 7.52 (1H, s), 7.58 (1H, d, J = 9.0 Hz), 7.61-7.74 (2H, m), 8.12 (1H, brs)

The synthetic route of 1017779-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
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Electric Literature of 116557-46-1, The chemical industry reduces the impact on the environment during synthesis 116557-46-1, name is 3-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

Step 5 To a reaction vial charged with 3-bromo-2-methoxyaniline from Step 4 (0.30 g, 1.485 mmol) and l-(l-ethoxyethyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- lH-pyrazole from Step 3 (0.435 g, 1.633 mmol) in dioxane (2 ml) was added aqueous potassium phosphate (2.0 M) (1.485 ml, 2.97 mmol). The resulting mixture was deoxygenated by bubbling argon through the mixture for ~5 min. PdCl2(dppf) (0.033 g, 0.045 mmol) was then added and the mixture was heated at 110 C for 3h then cooled to rt. The resulting mixture was diluted with EtOAc (100 mL), washed with water, brine, dried over anhyd sodium sulfate, filtered and concentrated to afford a black oil as the crude product mixture. This material was purified by silica gel flash chromatography using hexanes/ethyl acetate solvent mixtures as the eluant. Fractions containing the major uv active component were collected and combined then concentrated under vacuum to afford the desired product, Preparation 9 (355 mg, 1.358 mmol, 91%> yield) as an oil which solidified upon standing. HPLC (method N) RT = 1.58 min. LCMS (m+1) = 262.1.

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, 3-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, 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 658-89-9, Computed Properties of C7H7F3N2O

2-Methyl-5-trifluoromethoxybenzimidazole. The starting material, 2-amino-4-trifluoromethoxyaniline, was obtained by the method of Yagupolskii, L. M. et al. (Yagupolskii L. M., Troitskaya V. I. J. Gen. Chem. USSR Engl. Transl., 1961, Vol. 31, p. 845; Chem. Abstr. 1961, Vol. 55, p. 22830f). The procedure of Philips, M. A. (Philips M. A. J. Chem. Soc. 1929, p. 2820-2828) was used to produce 2-methyl-5-trifluoromethoxybenzimidazole. To 2-amino-4-trifluoromethoxyaniline (0.7 g, 0.0036 Mol) acetic acid anhydride (1.5g, 0.0146 Mol) was carefully added at 20 C. and the mixture was stirred 5 minutes at this temperature. Then 2-3 drops of concentrated aqueous HCl was added with stiffing, and the mixture was refluxed for 7 hours The reaction solution was cooled and diluted with water (10 mL), 0.5 g of charcoal was added, and the mixture was refluxed more 5-10 min. After cooling, the mixture was filtered and resulted clear filtrate was washed with ether (2×10 mL). The water layer was neutralized with excess of dilute NH4OH -(charcoal was filtered) The precipitate was filtered, washed with water and dried to give a solid (0.34 g, 44% by wt. pure). M.p. 135-137 C. 1H NMR (DMSO-d6): 2.49 (s, 3H), 7.17 (d, J=8.5 Hz, 1H), 7.34 (s, 1H), 7.62 (d, J=8.5 Hz, 1H). 13C NMR (DMSO-d6): 14.47, 107.44, 114.19, 117.25, 120.28 (q, J=255.2 Hz), 137.06, 139.46, 143.09, 153.26. 19F NMR (DMSO-d6): -57.41. [M+1]+ 217.

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; The United States of America as represented by the United States Department of Energy; US8242284; (2012); B1;,
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These common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, 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: 4-(Trifluoromethoxy)benzene-1,2-diamine

[0227] Quinoline-7-carboxylic acid (34.6 mg, 0.2 mmol, 1.0 equiv) and 4- trifluoromethoxy-l,2-diaminobenzene (40.3 mg, 0.21 mmol, 1.05 equiv) were suspended in dry Nu,Nu-dimethyl formamide (0.17 M) under argon atmosphere followed by the addition of triethylamine (1.2 equiv). Then HATU (N-[(Dimethylamino)-lH-l,2,3-triazolo-[4,5-b]pyridin-l- ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide) (1.2 equiv) was added and the reaction mixture was stirred for 16 hours at room temperature. After dilution with water, the mixture was extracted with dichloromethane (3 x 20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). Fractions containing the desired product were combined and solvent was removed in vacuo. Solid product was dissolved in glacial acetic acid (0.2 M) and the resulting solution was heated in a sealed vial at 140 C for 2 hours. After cooling down to room temperature, acetic acid was removed in vacuo and the crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). Fractions containing the desired product were combined and treated with saturated sodium bicarbonate solution. This mixture was extracted with dichloromethane (3 x 20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 47.5 mg of the desired product 74 as an off-white solid (38% yield) in >95% purity as determined by HPLC. 1H NMR (500 MHz; CD30D): delta 8.95 (dd, J = 4.3, 1.5 Hz, 1H), 8.71 (s, 1H), 8.43 (d, J = 8.2 Hz, 1H), 8.35 (dd, J = 8.6, 1.7 Hz, 1H), 8.13 (d, J = 8.6 Hz, 1H), 7.71 (d, J = 8.9 Hz, 1H), 7.61 (dd, J (0637) (s, 1H), 7.24 (d, J= 8.8 Hz, 1H); LC/MS [m/z]: 330 [M+H]+.

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

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
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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.

a-5-1) 1-tert-Butoxycarbonylamino-3,3-diethoxypropane A mixture of di-tert-butyl dicarbonate (9 g, 40 mmol.) in dioxane (40 ml) is added drop by drop, with stirring and at 0 C., to a solution of 1-amino-3,3-diethoxypropane (5.52 g, 37 mmol) and Et3N (4.04 g, 40 mmol) in 5 ml dioxane. After 2 hrs, the mixture is stirred at ambient temperature for 12 hrs then the solvent is evaporated. The residual oil is taken up in 10 ml of water, acidified with 30 ml HCl (1%), then extracted with ethyl acetate (60 ml*3). The organic phases are dried (MgSO4) and evaporated to give 8.89 g of 1-tert-butoxycarbonylamino-3,3-diethoxypropane (90%). 1H NMR (CDCl3): 1.20 (t, 6H, J=8.8 Hz, CH3), 1.40 (s, 9H, C(CH3)3), 1.60-2.00 (m, 2H, CH2C), 3.00-3.80 (m, 6H, OCH2+NHCH2), 4.50 (t, 1H, J=6.4 Hz, CH), 5.05-5.10 (br, 1H, NH).

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; Baudy Floc’h, Michele; Busnel, Olivier; Muller, Sylviane; US2011/44974; (2011); A1;,
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Reference of 7664-66-6, 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. 7664-66-6 name is 4-Isopropoxyaniline, 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.

To a mixture of 3-chloro-6-methyl-4-(4-methylbenzyl)pyridazine (200 mg, 0.859 mmol), 4-isopropoxyaniline (169 mg, 1.12 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (112 mg, 0.193 mmol), cesium carbonate (560 mg, 1.72 mmol) and dioxane (4 mL) was added palladium acetate (28.9 mg, 0.129 mmol) under nitrogen atmosphere, and the resulting mixture was heated at reflux for 1 hour. To the reaction mixture were added water (200 mL) and saturated aqueous ammonium chloride (5 mL). The resulting mixture was extracted with ethyl acetate (200 mL). The extract was washed by brine (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 3-(4-isopropoxyphenylamino)-6-methyl-4-(4-methylbenzyl)pyridazine (187 mg, Yield: 62.7%) as yellow amorphous. 1H-NMR (delta ppm TMS/CDCl3): 1.31 (6H, d, J=6.1 Hz), 2.37 (3H, s), 2.56 (3H, s), 3.84 (2H, s), 4.46 (1H, sep, J=6.1 Hz), 5.96 (1H, s), 6.80 (2H, d, J=8.3 Hz), 7.08 (2H, d, J=7.9 Hz), 7.18 (2H, d, J=7.9 Hz), 7.34 (2H, d, J=8.3 Hz).

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

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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