Tag: M.W=200-300

Electric Literature of 1036724-54-5, 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 1036724-54-5 as follows.

Six reactions were carried out in parallel and combined for work-up. To a solution of the product of the previous step (200 g, 711 mmol) in 15 THF (100 mL) was added 11 potassium carbonate (197 g, 1.4 mol). The reaction mixture was purged with nitrogen 3 times, followed by addition of Pd(dppf)Cl2-CH2Cl2 (11.6 g, 14.2 mmol). The reaction mixture was cooled to 0 C., diethylzinc (1 M, 1.07 L) was added drop-wise, and the reaction mixture was stirred at 70 C. for 1 h. The reactions were combined, cooled to 20 C. and poured into water (7 L) slowly. To the mixture was added aq. 4 M 16 HCl to pH 6. The organic layer was separated, and the aqueous phase was extracted with EtOAc (3×2 L). The combined organic layer was washed with brine (5 L), dried over sodium sulfate, concentrated, and purified through a silica gel pad (eluted with 50:1 17 petroleum ether:EtOAc)) to give the title intermediate (900 g, 92% yield) as a light yellow 18 oil. 1H NMR (400 MHz, CDCl3) delta 7.29-7.43 (m, 5H), 6.94-6.97 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.70 (m, 1H), 5.09 (s, 2H), 2.52-2.58 (m, 2H), 1.17 (t, J=7.6 Hz, 3H).

According to the analysis of related databases, 1036724-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22171-15-9, name is (4-(Benzyloxy)phenyl)methanamine, 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 22171-15-9, Recommanded Product: 22171-15-9

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.6g, 3.92mmol), triethylamine (1.64mL, 11.8mmol) and benzotriazole-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (2.6g, 5.9mmol) were dissolved in N,N-dimethylformamide (200mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (1.25g, 5.9mmol) was added thereto, and the solution was stirred at room temperature for 16 hours. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate : hexane = 2 : 1, then ethyl acetate), the resulting solid was washed with solvent (chloroform : ethyl acetate = 2 : 1), and the title compound (0.37g, 1.1 mmol, 27%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.29 (2H, d, J=6.0Hz), 5.07 (2H, s), 5.66 (1H, d, J=8.4Hz), 6.06 (2H, br s), 6.91-6.97 (4H, m), 7.19 (2H, d, J=8.8Hz), 7.29-7.45 (5H, m), 7.65 (1H, d, J=8.4Hz), 8.27 (1H, t, J=6.0Hz).

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-(Benzyloxy)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. Formula: C11H25NO2

Hexadecandioic acid (40.0 g, 140 mmol) was suspended in toluene (250 ml) and the mixture was heated toreflux. N,N-Dimethylformamide di-tert-butyl acetal (76.3 g, 375 mmol) was added drop-wise over 4 hours. The mixturewas refluxed overnight. The solvent was removed in vacuo at 50 C, and the crude material was suspended in dichloromethane/ethyl acetate (500 ml, 1:1) and stirred for 15 mins. The solids were collected by filtration and triturated withdichloromethane (200 ml). The filtrated were evaporated in vacuo to give crude mono-tert-butyl hexadecandioate, 30grams. This material was suspended in dichloromethane (50 ml), cooled with ice for 10 mins, and filtered. The solventwas removed in vacuo to leave 25 gram crude mono-tert-butyl hexadecandioate, which was recrystallized from heptane(200 ml) to give mono-tert-butyl hexadecandioate, 15.9 g (33 %). Alternatively to recrystallization, the mono-ester canbe purified by silica chromatography with ethyl acetate/heptane. 1H-NMR (CDCl3) delta: 2.35 (t, 2H), 2.20 (t, 2H), 1.65-1.55(m, 4H), 1.44 (s, 9H), 1.34-1.20 (m, 20 H).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; HOEG-JENSEN, Thomas; JAKOBSEN, Palle; SENSFUSS, Ulrich; FLEDELIUS, Christian; RIBEL-MADSEN, Ulla; (32 pag.)EP2448962; (2016); B1;,
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Reference of 886762-08-9, 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. 886762-08-9 name is 5-Bromo-2-(trifluoromethoxy)aniline, 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.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
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Reference of 43229-65-8, The chemical industry reduces the impact on the environment during synthesis 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, I believe this compound will play a more active role in future production and life.

1) A compound of the formula II (178.1 g) and a compound of the formula III (161.7 g) are added to a reaction flask and stirred.Heat to internal temperature 90-100 C, reaction 2-3h, to internal temperature 120-130 C, reaction 2-3h to complete(HPLC detection, the peak area is calculated according to the normalization method, and the compound of the formula III is less than 10%, the reaction is considered complete), and the compound of formula IV is obtained, 320.5g,After cooling to 70 ± 5 C, it was dissolved in anhydrous ethanol (220 mL) to prepare for the next step.

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, N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Health Yuan Breathe Pharmaceutical Engineering Co., Ltd.; Shanghai Fangyu Health Pharmaceutical Technology Co., Ltd.; Yu Xiong; Xiao Duzheng; Zheng Guangji; Chen Yuhua; Yuan Xilun; (28 pag.)CN109535027; (2019); A;,
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Electric Literature of 115929-62-9, These common heterocyclic compound, 115929-62-9, name is 3-Bromo-2,5-dimethoxyaniline, 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: In a round bottom flask equipped with a magnetic stirring bar, 0.3mmol of alpha-formyl-beta-carboline (1a) and 0.3mmol of aniline (2a) in 4mL of [Bmim][BF4] was stirred for 12min. Into this reaction mixture were added 0.35mmol of phenylacetylene (3a) and 10mol% of La(OTf)3 and then heated around 95-100C. After completion of the reaction, as indicated by the TLC, water was added and extracted with ethylacetate. The organic layer was dried over anhydrous Na2SO4. The solvent was concentrated under the reduced pressure. Product was purified by column chromatography on silica gel (eluent: Hexanes/ethyl acetate): Colorless solid, 126 mg, 74%, Rf=0.52 (20% EtOAc/Hexanes), mp: 277-279 C; IR (KBr): 3356, 2939, 2841, 1259, 1107, 744, 545 cm-1; 1H NMR (400 MHz, CDCl3, TMS) delta: 12.51 (1H, s), 9.01 (1H, s), 8.77 (1H, s), 8.28 (1H, d, J=7.7 Hz), 7.76-7.78 (1H, m), 7.69 (1H, t, J=7.4 Hz), 7.40-7.45 (6H, m), 6.99 (1H, s), 4.31 (3H, s), 4.08 (3H, s), 3.56 (3H, s); 13C NMR (100 MHz, CDCl3, TMS) delta: 166.7, 156.3, 153.2, 149.7, 147.2, 143.3, 141.9, 141.3, 137.3, 137.2, 136.9, 130.8, 129.2, 128.3, 127.2, 127.1, 122.1, 121.6, 121.3, 120.9, 119.0, 118.9, 116.7, 112.3, 110.3 (aromatic C), 61.6, 55.7, 52.6 (aliphatic C); HRMS (ESI-MS) calcd for C30H22BrN3O4; 590.0692 (M+Na), found: 590.0692. Anal. Calcd for: C, 63.39; H, 3.90; N, 7.39%; found: C, 63.25; H, 3.98; N, 7.21%.

Statistics shows that 3-Bromo-2,5-dimethoxyaniline is playing an increasingly important role. we look forward to future research findings about 115929-62-9.

Reference:
Article; Ramesh, Subburethinam; Nagarajan, Rajagopal; Tetrahedron; vol. 69; 24; (2013); p. 4890 – 4898;,
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Some common heterocyclic compound, 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, molecular formula is C13H14ClNO, 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. Product Details of 92028-21-2

To a flask containing 3.91 g (10 mmol) of compound B (Example 13, part b), 3.06 g (13 mmol) of 4-methoxy-3-phenylaniline hydrochloride (from TCI), 0.46 g (0.5 mmol) of tris(dibenzylidineacetone)dipalladium(0), 0.93 g (1.5 mmol) of racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and 2.21 g (23 mmol) of sodium tert-butoxide was added 50 mL of toluene, and the mixture was heated at 95 C. for 5.5 hours under an nitrogen atmosphere. The mixture was partitioned between 1.0 M aqueous NaHSO4 and diethyl ether, and the phases were separated. The diethyl ether phase was diluted with one volume of hexanes, and was washed once each with 1.0 M aqueous NaHSO4 and brine, dried over Na2SO4, filtered, and concentrated to a dark oil. The oil was purified by silica gel chromatography, using 12% EtOAc/88% hexanes as eluent, to give compound D as a yellow foam. 1H NMR (300 MHz, DMSO-d6) delta 7.76 (s, 1H), 7.38-7.13 (m, 10H), 6.95-6.81 (m, 7H), 4.28 (s, 2H), 3.61 (s, 3H), 3.16 (m, 2H), 2.53 (m, 2H), 1.29 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 92028-21-2, its application will become more common.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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. COA of Formula: C9H10BrFO2

4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene (87.0 g, 349.27 mmol) was dissolved in THF (700 mL) and cooled to -78 C. n-Butyl lithium (185.42 mL of a 2.5 M soln in hexanes, 461.04 mmol) was rapidly added and immediately followed by addition of DMF (40.40 mL, 523.91 mmol). Reaction was stirred in the cold for 30 min then allowed to warm to rt and stirred for 1 h. The reaction solution was diluted with H2O (500 mL) and extracted with Et2O (3*500 mL). The combined organic extracts were washed with brine (3*200 mL), dried (Na2SO4), filtered, concentrated and chromatographed (eluted with 10% EtOAc in hexanes) to provide 45.90 g of 4-(dimethoxymethyl)-3-fluorobenzaldehyde as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 439814-87-6, its application will become more common.

Reference:
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
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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 13070-45-6 as follows. HPLC of Formula: C13H15NO

Dissolve 93 mg of S11 in acetonitrile.Add 135 mg of 3,4-dihydroxybenzonitrile and add 7 mg of iron phthalocyanine under ice bath.30 mg of acetic acid, 4.8 mg of methanesulfonic acid and 135 mg of tert-butyl hydroperoxide, After stirring the reaction for 5 minutes under the same conditions,After monitoring the reaction, it was diluted with 20 mL of ethyl acetate and extracted with 20 mL of H2O.The combined organic layer Wash with 20 mL of saturated brine.Dry with anhydrous Na2SO4, filter and spin dry. Purified with silica gel column, eluent PE/ EtOAc = 8:1,188 mg of compound 11,The reaction yield was 56%;The product was a light yellow oil at room temperature.Physical state: light yellow oil; melting point: 138.5-139.4 C

According to the analysis of related databases, 13070-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fuzhou University; Chen Haijun; Guo Mei; Ye Jinxiang; Chen Yi; Lin Yuqi; Gao Yu; (14 pag.)CN108530456; (2018); 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 588-96-5 as follows. name: p-Bromophenetole

General procedure: In air, aryl halide (0.2 mmol), arylboronic acid (0.22 mmol),K2CO3 (0.3 mmol), 5 ml of distilled water, and 2 mg of catalystwere combined in a 10 ml round bottom flask. The reactionmixture was magnetically stirred and the temperature wasmaintained at 75 C in an oil bath. Reaction progress was monitoredby TLC. After reaction was completed, the reaction mixturewas cooled to room temperature and filtrated. The filtratedsolid was washed with water (35 ml) and dissolved withethyl acetate. The catalyst was separated by filtration, washedwith water, and dried in vacuum. The combined organic phasewas dried with anhydrous MgSO4, and the solvent was removedunder reduced pressure to give the product.

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ma, Hengchang; Bao, Zhikang; Han, Guobin; Yang, Ningning; Xu, Yufei; Yang, Zengming; Cao, Wei; Ma, Yuan; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 3; (2013); p. 578 – 584;,
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