Author: Jessica.F

Related Products of 16429-44-0, A common heterocyclic compound, 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

5-Bromo-3-chloro-1 ,2-diaminobenzene (4.6 g; 20 mmol; 1 eq.) is dissolved in EtOH (200 mL) and 2,3-dixydroxy-1 ,4-dioxane (2.5 g, 20 mmol; 1 eq.) is added. The mixture is stirred for 4 h at room temperature and a second portion of 2,3-dihydroxy-1 ,4-dioxane (1.3 g; 10 mmol; 0.5 eq.) is added. After stirring for 24 h at room temperature, the reaction mixture is concentrated and the residue is purified by FCC (EtOAc gradient in hexane) to provide 7- bromo-5-chloroquinoxaline as a beige solid (4.7 g; yield: 92%; UPLC purity: 98%).

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; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1298031-94-3,Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 mixture of 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.2 g, 4.9 mmol), cyclopropylboronic acid (843 mg, 9.8 mmol), Pd(dppf)Cl2 (359 mg, 0.49 mmol) and Na2C03 (1.56 g, 14.7 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was stirred at 90 C under N2 for 48 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 6-chloro-8-cyclopropyl-2- methylimidazo[l,2-b]pyridazine (405 mg, 40%). MS m/z 208.0, 210.0 [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 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7ClFN

3-Chloro-5-fluorobenzylamine (97 mg, 0.61 mmol) and Et3N (0.24 ml, 1.8 mmol) followed by T3P (0.6 ml, 1.8 mmol) are added at 0 C. to a solution of 3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (150 mg, 0.61 mmol) in 5 ml of dichloromethane. The reaction mixture is stirred at room temperature under nitrogen for 4 hours. When the reaction is complete, water is added, and the mixture is extracted to exhaustion with dichloromethane. The combined organic phases are subsequently washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation, the residue is purified by chromatography on silica gel, giving the product as colourless solid (150 mg, 63% yield); Thin-layer chromatogram: chloroform/methanol=9.5:0.5), Rf: 0.3 LC/MS: 388.1 (M+H at 1. 388 min); HPLC: Rt 5.12 min (HPLC purity 95.15%, 95.46%); 1H NMR (DMSO-d6, 400 MHz): delta [ppm] 9.13 (t, J=6.08 Hz, 1H), 7.70-7.68 (m, 2H), 7.43 (t, J=8.64 Hz, 2H), 7.32-7.29 (m, 1H), 7.24-7.20 (m, 2H), 7.09 (d, J=9.80 Hz, 1H), 4.42-4.34 (m, 2H), 3.95-3.89 (m, 2H), 2.61-2.58 (m, 1H), 2.28-2.22 (m, 1H).

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 90390-33-3.

Reference:
Patent; Merck Patent GmbH; Heinrich, Timo; Zenke, Frank; Calderini, Michel; Musil, Djordje; US2013/296274; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1009102-44-6, These common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, 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.

In step 1 Manufactured 1-(4-chlorophenyl)cyclopropan-1-amine hydrochloride (0.500 g, 2.450 mmol), ethyl 2-chloropyrimidine-5-carboxylate (0.503 g, 2.695 mmol) and N,N-diisopropylethylamine (1.280 mL, 7.350 mmol) was dissolved in 1,4-dioxane (10 mL) at room temperature and stirred at 110 C for 18 hours, and then the temperature was lowered to room temperature to complete the reaction. After the solvent was removed from the reaction mixture under reduced pressure, the concentrate was crystallized from ethanol (5 mL) at room temperature, filtered and washed with ethanol and dried to give the title compound (0.520 g, 66.8%) as a white solid.

The synthetic route of 1009102-44-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8, These common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, 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 13 1-(5-Chloro-3-trifluormethyl-anilino)-4-(4-pyridyl-methyl)-phthalazine A suspension of 27.9 g (109 mMol) of 1-chloro-4-(4-pyridyl-methyl)-phthalazine (Example 67A.1 in WO 98/35958) and 21.4 g (109 mMol) of 5-amino-3-chloro-benzotrifluoride (Example 5b) in 500 ml of ethanol and 27.4 ml of 4 N HCl/dioxane is stirred during 3 h a 80 C. After cooling down, the reaction mixture is diluted with 0.3 l of ether, filtrated, and washed with ether. The remaining solid is then taken up in water and EtOAc, brought to alkaline pH by means of NH3 solution, stirred for 15 min at room temperature and then filtered and washed with ether (?raw product). The water layer is removed from the filtrate and extracted twice with ethyl acetate. The organic layers are washed with water and brine, dried over Na2SO4 and evaporated. The residue is combined with the raw product mentioned above, and the solid is dissolved in ethyl acetate and methanol. About 100 g SiO2 are added, followed by evaporation, and the powder is applied onto a silica gel column and eluted with ethyl acetate and subsequently with a mixture of ethyl acetate and methanol (98:2?95:5, v/v). Solving the obtained fractions in ethyl acetate/methanol, partial evaporation and crystallization by addition of ether/hexane leads to the title compound: m.p. 231-232 C.; An. calc. (C21H14N4ClF3) C, 60.81%; H, 3.40%; N, 13.51%; Cl, 8.55%; F, 13.74%; An meas. C, 60.8%; H, 3.4%; N, 13.5%; Cl, 8.5%; F, 13.8%; 1H-NMR (DMSO-d6) 9.63 (s, HN), 8.60 (d, 1H), 8.56 (s, 1H), 8.44 (d, 2H), 8.39 (s, 1H), 8.16 (d, 1H), 8.03 (t, 1H), 7.97 (t, 1H), 7.43 (s, 1H), 7.32 (d, 2H), 4.63 (s, 2H); FAB-MS (M+H)+=415.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bold, Guido; Dawson King, Janet; Frei, Jorg; Heng, Richard; Manley, Paul William; Wietfeld, Bernhard; Wood, Jeanette Marjorie; US2003/13718; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000577-58-1, name is 1-Bromo-2,3-dichloro-5-fluorobenzene, belongs to chlorides-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 1000577-58-1, Recommanded Product: 1000577-58-1

A mixture of l-bromo-2,3-dichloro-5-fluorobenzene (3.1304 g, 12.94 mmol), bis(pinacolato)diboron (5.7397 g, 22.38 mmol), potassium acetate (3.9788 g, 40.1 mmol) in DMSO (60 mL) was stirred at room temperature for about 30 min. The mixture was degassed with nitrogen for a few minutes and l ,l’-[bis(diphenylphosphino)ferrocene]dichloro- palladium (II) (0.7953 g, 1.09 mmol) was added. The mixture was degassed again with nitrogen, was heated to 80 oc with stirring and kept at 80 oC for 4 h 20 min. The mixture was cooled to room temperature and poured into ice. The mixture was extracted with ethyl acetate (3 x 150 mL). The combined organic solution was washed with saturated sodium chloride solution (150 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was separated with flash column chromatography on silica gel using ethyl acetate/hexane to afford product as white solid (2.6156 g, Yield: 70%). NMR (500 MHz, Chloroform-d) delta 7.070 (d, J= 3.0 Hz, lH), 7.029 (d, J= 3.0 Hz, 1H), 1.238 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3-dichloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT. LTD.; NEKTAR THERAPEUTICS; SHARMA, PANKAJ; KHATRI, VIJAY KUMAR; GU, XUYUAN; SONG, YUAN; SHEN, MICHAEL LIXIN; SAUTHIER, JENNIFER RIGGS; ANAND, NEEL K.; KOZLOWSKI, ANTONI; ODINECS, ALEKSANDRS; RILEY, TIMOTHY A.; REN, ZHONGXU; MU. YONGQI; SHEN, XIAOMING; YUAN. XUEJUN; AURRECOECHEA, NATALIA; O’MAHONY, DONOGH JOHN ROGER; WO2015/92819; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 348-65-2, name is 5-Chloro-2,4-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Chloro-2,4-difluoroaniline

j00283j A solution of 5-chloro-2,4-difluoro-aniline (5.0 g, 31 mmol) and potassium 0-ethyl carbonodithioate (12 g, 73 mmol) in 1V N-dimethylformamide (50 mL) was stirred at 130 C for 16hours. On completion, the reaction was cooled to room temperature, and iN hydrochloric acid (100 mL) was added. The mixture was stirred for 1 hour, resulting in formation of a solid. The solid was collected by filtration, washed with water (2×100 mL) and dried under vacuum to give compound B- 5(5.6 g, 79% yield) as a white solid. LCMS (B): tR=0.759 mi, (ES)m/z(M+H)=220.1.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 29027-17-6, These common heterocyclic compound, 29027-17-6, name is 2-Chloro-3-methylaniline, 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-Chloro-1-isothiocyanato-3-methylbenzene To 2-chloro-3-methylaniline (1 equiv.) in DCM/water (0.5 M, 1/2) at 0 C. was added NaOH (3 equiv.), the solution was stirred at 0 C. for 5 min, then CSCl2 (3 equiv.) was added. The reaction was stirred at room temperature overnight. The reaction was extracted with DCM. The combined organic layers were concentrated to dryness to give crude 2-chloro-1-isothiocyanato-3-methylbenzene. The crude product was purified by column chromatography on silica gel with petroleum ether to give 2-chloro-1-isothiocyanato-3-methylbenzene (61%) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta ppm: 7.19-7.09 (m, 3H), 2.42 (s, 3H).

Statistics shows that 2-Chloro-3-methylaniline is playing an increasingly important role. we look forward to future research findings about 29027-17-6.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 69411-05-8 as follows. Quality Control of 3-Chloro-5-trifluoromethylaniline

Intermediate E (120 mg, 0.25 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (49 mg, 0.27 mmol) and DMAP (16 mg, 0.125 mmol) were dissolved in THF (15 mL). The reaction mixture was heated to 85 C for 16 hours. The solvent was removed and the crude product was purified by column chromatography (DCM: methanol 100/0 to 98/2) to give 5-((4-((4-(3-(3-chloro-5- (trifluoromethyl)phenyl)ureido)phenyl)(methyl)amino)pyrimidin-2-yl) amino)-N,2- dimethylbenzamide (38 mg, 26%) as a white solid. LCMS (method B): 2.74 min [MH]+=584.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.23 (s, 3 H) 2.74 (d, J=4.8 Hz, 3 H) 3.41 (s, 3 H) 5.77 (d, J= 7.0 Hz, 1 H) 7.07 (d, J= 8.4 Hz, 1 H) 7.28 (d, J= 8.8 Hz, 2 H) 7.43 (s, 1 H) 7.59 (d, J= 8.8 Hz, 2 H) 7.67 (dd, J=8.4 2.0 Hz, 1 H) 7.87 (m, 4 H) 8.11 (m, 1 H) 9.15 (s, 1 H) 9.19 (s, 1 H) 9.37( s, 1 H).

According to the analysis of related databases, 69411-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

To 150 mL of DMF (dimethylformaldehyde), 1,3-dibromo-2-chloro-5-fluorobenzene (23.0 g, 79.8 mmol), dimethylamine (24.3 g, 144 mmol) and cesium carbonate (84.4 g, 239 mmol) were added thereto, and the mixture was heated to 140 C and reacted for 40 hours. After cooling to room temperature, the mixture was extracted with EA, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. This was subjected to column chromatography with EA: Hx to obtain 12.0 g (Yield = 34%) of [Intermediate 7-1].

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; LG Chem, Ltd.; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Yoon Jeong-min; Lee Hyeong-jin; Kim Gong-gyeom; (57 pag.)KR2018/112722; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics