Author: Jessica.F

Some common heterocyclic compound, 95970-08-4, name is 2,5-Dibromoanisole, molecular formula is C7H6Br2O, 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: C7H6Br2O

(0957) [00336] Into a lOG-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added l,4-dibromo-2-methoxybenzene (2.60 g, 9.78 mmol), benzyl piperazine- 1-carboxylate (2.37 g, 10.8 mmol), Pd2(dba)3-CHCij (0.508 g, 0.490 mmol), XantPhos (0,583 g, 0.980 mmol), and NaOtBu (2.82 g, 29.3 mmol) followed by toluene (40 mL). The reaction mixture was stirred, for 3 h at 80 C and then concentrated in vacuo. The resulting crude product was purified by FCC eluting with ethyl acetate/petroleum ether (1 : 10) to afford benzyl 4-(4- (0958) 131 (0959) 144628010 vl bromo-3-methoxyphenyl)piperazine-l-carboxylate as a brown solid (2 g, 50%). LCMS (ESi, m/z): 405, 407 [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 95970-08-4, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
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These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. Recommanded Product: 111-95-5

Example 6 N4,N4-bis(2-methoxyethyl)-1-methyl-N-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide A suspension of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-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 1N aqueous hydrochloric acid, once with brine, dried with magnesium sulfate and the solvent is evaporated to dryness affording N4,N4-bis(2-methoxyethyl)-1-methyl-N-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (80 mg, 84.8%) as a colorless waxy solid. MS: m/z=478.2 (M+H+).

The synthetic route of Bis(2-methoxyethyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Flohr, Alexander; Gobbi, Luca; Groebke Zbinden, Katrin; Koerner, Matthias; Peters, Jens-Uwe; US2012/142665; (2012); A1;,
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Related Products of 93919-56-3, 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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4- (trifluoromethoxy) benzylamine (3.46 g, 57.6 mmol) in DMF (75 mL) and acetic acid (10.0 g, 52.3 mmol) at-10 C were added 0- (BENZOTRIAZOL-1-YL)-N, NN’, N’- tetramethyluronium tetrafluoroborate (20.2 g, 62.8 mmol) and NN-DIISOPROPYLETHYLAMINE (20.0 mL, 115 mmol) and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 ML) was added and the organic phase was washed with water (100 mL), 0.25 M NAOH (100 mL), saturated aqueous NAHCO3 (100 ML), water (100 mL), 0.5 M HCl (100 ML), and water (100 ML), dried over MgS04, and concentrated in vacuo to afford 11.2 g (92%) of a colourless oil. ‘H NMR (600 MHz, CDC13) : 8 2.03 (s, 3H), 4.43 (d, 2H), 5.83 (bs, 1H), 7.17 (d, 2H), 7.31 (d, 2H). 13C NMR (125 MHZ, CDC13) : 8 22.9, 42.8, 120.5 (q), 121.1, 129.0, 137.3, 148.4, 170.6.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/56748; (2004); A1;,
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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. 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C11H16N2O2

[0567] A solution of7 -( dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 4, 2 g, 9.60 mmol) anddiphenylcarbonate ( 4.11 g, 19.21 mmol) in THF ( 40 ml) at-15 C. was treated with LHMDS (1M in THF, 13.3 ml, 13.3mmol) over 0.5 h. The reaction mixture was quenched withsat. aq. NH4Cl, extracted with EtOAc (2x). The combinedorganic layers were washed with brine, dried over Na2S04 ,filtered and concentrated under reduced pressure. The crudeproduct was purified by normal phase chromatography (80 gsilica gel cartridge, heptanes/EtOAc 100:0 to 25:75) to givethe title compound as a pale yellow solid. 1H-NMR (400MHz, DMSO-d6 ) o7.65 (d, lH), 7.46-7.38 (m, 2H), 7.27-7.18 (m, 4H), 5.17 (s, lH), 3.87-3.80 (m, 2H), 3.26 (s, 6H), 2.83(t, 2H), 2.00-1.92 (m, 2H).

The synthetic route of 204452-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Buschmann, Nicole; Fairhurst, Robin Alec; Furet, Pascal; Knoepfel, Thomas; Leblanc, Catherine; Liao, Lv; Mah, Robert; Nimsgern, Pierre; Ripoche, Sebastien; Xiong, Jing; Han, Bo; Wang, Can; Zhao, Xianglin; US2015/119385; (2015); 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 175278-09-8 as follows. Formula: C7H5BrF3NO

A solution of 8 g (31 mmol) of 4-bromo-2-trifluoromethoxyaniline and 4.2 g (37.5 mmol) of DABC (triethylenediamine) in 40 mL of toluene was slowly added dropwise 7 mL of carbon disulfide and the reaction was stirred at room temperature 8h. After the reaction, the reaction solution was suction filtered, and the filter cake was 3g of [4-bromo-2-trifluoromethoxyphenyl] dithioic acid with a yield of about 28%.

According to the analysis of related databases, 175278-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Jiao Tong University; He, LangChong; Zhang, Jie; Pan, XiaoYan; Wang, Jinfeng; Su, Ping; Lu, Wen; Wang, Sicen; (17 pag.)CN105924385; (2016); A;,
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Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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. Quality Control of 4-Bromo-3-methoxyaniline

Step 1: 6-Bromo-7-methoxyquinoline In a 100 mL round-bottom flask, a solution of concentrated sulfuric acid (2.1 mL, 39.6 mmol) in water (2.4 mL) was treated with 3-nitrobenzenesulfonic acid (2.06 g, 10.1 mmol) and glycerol (2.5 mL, 34.8 mmol) to give a thick grey suspension. The mixture was heated to 110 C. (oil bath) and 4-bromo-3-methoxyaniline (1.952 g, 9.66 mmol) was added portion-wise, resulting in an immobile slurry. Additional portions of water (3 mL), glycerol (3 mL), and concentrated sulfuric acid (3 mL) were added and the temperature increased to 140 C. After three hours the mixture had become a homogeneous dark brown solution, and LCMS analysis indicated reaction completion. The solution was cooled to RT, poured onto ice, and the pH was adjusted to 8 by addition of concentrated (30%) aqueous ammonium hydroxide. The mixture was partitioned between ethyl acetate and water, washed with water, brine, dried over magnesium sulfate and concentrated to a brown liquid. Purification by flash column chromatography (24 g silica gel, gradient of 0-20% ethyl acetate in dichloromethane over 25 column volumes) provided 6-bromo-7-methoxyquinoline (1.18 g, 46.2%) as a light brown fluffy solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.86 (dd, J=4.0, 1.5 Hz, 1H), 8.01-8.12 (m, 2H), 7.53 (s, 1H), 7.34 (dd, J=8.1, 4.5 Hz, 1H), 4.07 (s, 3H). NMR indicates the presence of about 10% 7-methyoxyquinoline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; AXFORD, Jake; DALES, Natalie; SUNG, Moo Je; US2014/206661; (2014); 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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Bromo-2,2-dimethoxypropane

Pentafluorophenoxyacetone, 39 Pentafluorophenol (1 g, 5.5 mmol), 1-bromo-2,2-dimethoxypropane (1 g, 5.5 mmol) and tetrabutylammoniun hydrogen sulfate (1.86 g, 5.5 mmol) phase transfer catalyst were dissolved in CH2 Cl2 (30 ml). KOH (2.8 g, 50 mmol) dissolved in H2 O (30 ml) was added. The reaction mixture was stirred at room temperature for two days. The organic layer was washed with 10% HCl (during this procedure the acetal was hydrolyzed to the product ketone), 10% NaHCO3 and H2 O. The product was separated from unreacted starting material by flash chromatography on silica gel (ethyl acetate/hexane 25/75), yielding 0.16 g. (12%) of a colorless liquid. 1 H NMR (CDCl3): delta2.32 (s, 3H, methyl group) 4.78 (s, 2H, methylene group).

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 126-38-5.

Reference:
Patent; Northeastern University; US5360819; (1994); A;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8F3NO

Step 4; 5-(2-phenyl-6-(4-(trifluoromethoxy)benzylcarbamoyl)qumolin-3-yl)pentanoic acid trifl oroacetate; To a solution of 1C (51 mg, 0.126 mmol) in DCM (5 mL) was added HATU (72 mg, 0.189 mmol) followed by DIPEA (81.3 mg, 0.629 mmol) and 4- (trifluoromethoxy)benylamine (38 uL, 0.25 mmol). The reaction mixture stirred at RT for 1 h. The reaction mixture was treated with TF A (3 mL), stirred at RT for 2 h and then concentrated to dryness under reduced pressure. Chromatography (5-100% EtOAc/hexanes) provided 1 (74 mg; Yield – 92%, LCMS (M+H) = 523).

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:
Patent; MERCK SHARP & DOHME CORP.; SCHERING CORPORATION; BOYCE, Christopher, W.; FEVRIER, Salem; MCCORMICK, Kevin, D.; PALANI, Anandan; ASLANIAN, Robert, G.; SILIPHAIVANH, Phieng; METHOT, Joey, L.; BROWN, William Colby; VACCARO, Henry; WO2012/87872; (2012); A1;,
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Reference of 5397-31-9, A common heterocyclic compound, 5397-31-9, name is 3-((2-Ethylhexyl)oxy)propan-1-amine, molecular formula is C11H25NO, 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 1 Red Complex from Reactive Red 120, 3-(2-Ethylhexyloxyl)Propylamine and Aliquat 336 (0102) 14.7 gram of Reactive Red 120 (50% dye content), 2.81 gram of 3-(2-ethylhexyloxy)-propyl amine, 0.84 gram of sodium bicarbonate and 30 mL of water were charged into a reactor equipped with agitator, temperature control and condenser. The mixture was heated to 80 C. for several hours until the starting material Reactive Red 120 was gone as monitored by TLC. Then 12.1 gram of Aliquat 336 was added slowly and stirred at 80 C. for one hour. The reaction mixture was cooled to room temperature and dark red solid was precipitated. The solid was filtered and washed with water to remove salts. 24.1 gram of red solid with color value of 12.8 was obtained.

The synthetic route of 5397-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milliken & Company; Hong, Xiaoyong Michael; Xie, Peter; Sun, Brian; Mason, Mary E.; US2015/299468; (2015); A1;,
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Electric Literature of 22236-08-4, A common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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: A solution of cyanic bromide [Caution, highly toxic] (2 equiv) in diethyl ether (10 mL) was added dropwise to a solution of the appropriately substituted aniline (1 equiv) in diethyl ether (10 mL) at 0 C. After complete addition the mixture was warmed to ambient temperature and stirred 1-20 h, which was followed by TLC. Solids were filtrated and washed with ether. The filtrate was washed with 1 M HCl (25 mL) followed by brine (25 mL). The organic layer was collected, dried over anhydrous MgSO4, filtrated and evaporated to dryness under reduced pressure. 5.1.32 N-(3-(Difluoromethoxy)phenyl)cyanamide (24h) The reaction of 3-(difluoromethoxy)aniline (23h) (1.60 g, 10.0 mmol) according to procedure A yielded, after purification over silica with ethyl acetate/petroleum ether (60-80) (25/75, v/v), the title compound as a light brown oil which solidified upon standing (683 mg, 3.71 mmol, 37%); Rf 0.24 (ethyl acetate/petroleum ether (60-80), 25/75, v/v). 1H NMR (CDCl3) delta 7.31-7.22 (m, 2H, HAryl), 6.87-6.76 (m, 2H, HAryl), 6.77 (s, 1H, NH), 6.48 (t, JHF = 73.5 Hz, 1H, CHF2). 13C NMR (CDCl3) delta 152.30 (Ar-O), 138.96 (Ar-N), 131.18 (Ar), 117.84 (t, CHF2, JCF = 260.72 Hz), 114.37 (Ar), 112.48 (Ar), 111.13 (NCN), 107.24 (Ar).

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Klein, Pieter J.; Christiaans, Johannes A.M.; Metaxas, Athanasios; Schuit, Robert C.; Lammertsma, Adriaan A.; Van Berckel, Bart N.M.; Windhorst, Albert D.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1189 – 1206;,
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