Tag: M.W=100-200

These common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, 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. Product Details of 2106-02-7

Into a 20-L 4-neck round flask was placed a solution of 2-chloro-4- fluorobenzenamine (1300 g, 8.82 mol, 1.00 equiv, 99%) in toluene (10 L), 4- methylbenzenesulfonic acid (3.1 g, 17.84 mmol, 99%), and hexane-2,5-dione (1222.5 g, 10.62 mol, 1.20 equiv, 99%). The resulting solution was heated to reflux for 1 h in an oil bath and cooled. The pH value of the solution was adjusted to 8 with sodium carbonate (1 mol/L). The resulting mixture was washed with 1×5000 mL of water and concentrated under vacuum. The crude product was purified by distillation and the fraction was collected at 140 0C to afford l-(2- chloro-4-fluorophenyl)-2,5-dimethyl-lH-pyrrole (1700 g, yield: 85%).

The synthetic route of 2-Chloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; WENGLOWSKY, Steven Mark; WO2011/25947; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, 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: 2-Chloro-4-fluorobenzylamine

Example 82; /V-[(2-chloro-4-fluorophenyl)methyl]-2-[3,5-dimethyl-1-(2-phenylethyl)- 1H-pyrazol-4-yl]acetamide (E82)[3,5-dimethyl-1-(2-phenylethyl)-1 H-pyrazol-4-yl]acetic acid (0.63 mmol) was dissolved in dimethylformamide (2 ml) and to this was added O-(7-Azabenzotriazol- 1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU, 0.63 mmol) and diisopropylethylamine (DIPEA, 1.26 mmol). The mixture was left to stand at room temperature for 15-20 minutes and then [(2-chloro-4-fluorophenyl)methyl]amine (0.63 mmol) in dimethylformamide (1 ml) was added. The mixture was left to stand overnight at room temperature and then the solvents were evaporated in-vacuo. The residue was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The mixture was then filtered through a phase separator and the organic phase was evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give the title compound as product after lyophilisation of the combined product fractions. LC/MS [M+H]+ = 399, retention time = 3.16 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15205-11-5, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/138876; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 870-24-6, 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. 870-24-6, name is 2-Chloroethanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

13.5 g of 2-chloroethylamine hydrochloride was added to 8.7 g of mercaptoethanol solution under stirring, adjusted to pH=4.8, and reacted at 55 C. for 4 hours to produce 13.2 g.beta-2-aminoethylmercaptoethan-1-ol. Cooling to 0C,Slowly add 59g (40%) of tidal acetaminophenone chloride, adjust pH=3.8, control temperature at 0-2C for 4 hours, separate,Washing afforded 30.7 g of p-acetamidobenzenesulfonamide ethyl-2-hydroxyethyl sulfide

The chemical industry reduces the impact on the environment during synthesis 2-Chloroethanamine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taixing Jinyun Dyeing Liao Co., Ltd.; Zhao Weiguo; Su Jinqi; Ju Suhua; Wang Guomin; Zhang Weiping; (27 pag.)CN104592786; (2017); B;,
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 112581-77-8 as follows. Recommanded Product: 2,6-Dichloroimidazo[1,2-b]pyridazine

Reference Example 1 Into a 500 mL four-necked separable flask purged with nitrogen, 20.17 g of 2,6-dichloroimidazo[1,2-b]pyridazine (content: 99.2% by weight) and 190.5 g of xylene were charged to prepare a xylene solution containing 2,6-dichloroimidazo[1,2-b]pyridazine. The solution obtained by mixing 4 mL of xylene and 0.22 g of 1,3-bis(diphenylphosphino)propane and 0.62 g of a toluene solution of nickel naphthenate (II) (content: 5% by weight) were mixed to prepare a solution containing a nickel catalyst. The xylene solution containing 2,6-dichloroimidazo[1,2-b]pyridazine and the solution containing a nickel catalyst were mixed, and to the resultant mixture, 63.4 g of a tetrahydrofuran solution of n-propylmagnesium bromide (content: 22.2% by weight) was added dropwise over about 2 hours at an inner temperature of 20 to 30C to effect reaction. After completion of the reaction, the reaction mixture was added dropwise into a mixture of 40.4 g of 3% by weight aqueous sulfuric acid solution and 1 g of Radiolite (which was manufactured by Showa Chemical Industry Co., LTD.). After that, the resultant mixture was stirred and filtrated. The organic layer was separated from the filtrate obtained and washed twice with about 40 g of water. The organic layer after washing was concentrated to obtain 20.9 g of 6-n-propyl-2-chloroimidazo[1,2-b]pyridazine (purity: 93.2%). Yield: 94%

According to the analysis of related databases, 112581-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1932846; (2008); A1;,
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. 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-N-methylethanamine hydrochloride

Water (0.5 mL), intermediate 17 (0.17 g; 0.51 mmol) followed by tetrabutylammonium bromide (41 mg; 0.13 mmol) were added at room temperature to a mixture of potassium hydroxide (0.50 g; 7.63 mmol) in 2-methyltetrahydrofuran (5 mL). The reaction mixture was stirred for 10 minutes at room temperature, then stirred at 50C for 1 hour and (2- chloroethyl)-methylamine hydrochloride (CAS 4535-90-4) (0.119 g; 0.92 mmol) was added. The reaction mixture was stirred for 24 hours at 50C. The reaction mixture was cooled down to room temperature, poured into water and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (Spherical SiOH, 10muiotaeta, 60g; mobile phase: gradient from 0.5% NH4OH, 97% DCM, 3% MeOH to 0.5% NH OH, 95% DCM, 5% MeOH). The pure fractions were collected and evaporated to give 30 mg (15%) which was taken up Et20 and evaporated to give 29 mg (14%) of compound 44 , MP.: 80C (gum, Kofler).

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; ASTEX THERAPEUTICS LIMITED; BERDINI, Valerio; SAXTY, Gordon; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; ROUX, Bruno; MEERPOEL, Lieven; WO2013/61080; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2613-34-5, 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. 2613-34-5, name is 3-Chloro-2,4-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2- yl)sulfamoyl)-1H-pyrrole-2-carboxylic acid (450 mg, 1.43 mmol) and 3-chloro-4,5- difluoroaniline hydrochloride (0.57 g, 2.86 mmol) (synthesis described in synthesis for compound 57) and HATU (0.73 g, 1.91 mmol) were dissolved in DMF (2 mL) containingdiisopropylethylamine (0.82 mL, 4.77 mmol). The reaction mixture was stirred at 40C for 66 hours. The reaction mixture was directly loaded on column. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combined and evaporated to keep 50 mL of solvent. The precipitates were filtered and washed with petroleum ether and dried in vacuum oven at 50C overnight to affordcompound 137 (490 mg) as white powder.(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2-yl)sulfamoyl)- 1 H-pyrrole-2-carboxylic acid (168mg, 0.53 mmol) (synthesis described in synthesis for compound 137) 5-amino-2-fluorobenzonitrile (0.15 g, 1.07 mmol) and HATU (0.24 g, 0.64 mmol) were dissolved in DMF (1 mL) containing diisopropylethylamine (0.23 mL, 1.34 mmol). The reaction mixture was stirred at 50C for 1 hour. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combinedand evaporated to keep 50 mL of the solvent. The white solids were filtered and dried invacuum oven to afford compound 140 (180 mg) as white powder.Compound 143 (147 mg) as white powder was synthesized similarly as described for compound140 using 3-chloro-2,4-difluoroaniline (0.17 g, 1.07 mmol) instead of 5-amino-2-fluorobenzonitrile. The reaction mixture was stirred at 60C for 2 hours more. Method B; Rt:1.07 mi mlz: 458 (M-H) Exact mass: 459.04. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.09 (d,J7.0 Hz, 3 H), 2.44 (s, 3 H), 3.82 (s, 3 H), 3.76 – 3.91 (m, 1 H), 7.34 (td, J=9.0, 2.0 Hz, 1 H),7.35 (s, 1 H), 7.52 (td, J8.7, 5.8 Hz, 1 H), 8.20 (br. s., 1 H), 10.05 (s, 1 H).

The synthetic route of 3-Chloro-2,4-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 72235-58-6,Some common heterocyclic compound, 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, molecular formula is C7H7ClFN, 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.

Step 3: Intermediate 201 OB (50 mg, 0.16 mmol) is dissolved in DMF (2.0 ml_), then diisopropylethylamine (1 10 muIota_, 0.63 mmol, 4.0 eq) and 4-chloro-3-fluorobenzylamine ( Oakwood) (30 mg, 0.19 mmol, 1 .2 eq) are added followed by HATU (78 mg, 0.21 mmol, 1 .2 eq) and the reaction mixture is stirred at RT. Following completion of the reaction, the solution is filtered and purified by preparative HPLC to provide compound 2010 (tR: 1 .71 , (M+H)+: 459.2/461 .2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Chloro-3-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Product Details of 72235-58-6

A mixture of Example 235G (40.0 mg, 0.112 mmol), HATU (1- [bis(dimethylamino)methylene]-lH-l ,2,3-triazolo[4,5-]pyridinium 3-oxid (1666) hexafluorophosphate) (51.0 mg, 0.134 mmol), (4-chloro-3-fluorophenyl)methanamine (0.015 mL, 0.123 mmol), and triethylamine (0.031 mL, 0.224 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over MgSO/t, filtered, and concentrated. The residue was purified by HPLC performed on a Phenomenex Luna C18 column (250 x 30 mm, 10 mupiiota particle size) using a gradient of 20% to 100% acetonitrile:0.1 % aqueous trifluoroacetic acid over 26 minutes at a flow rate of 50 mL/minute to provide the title compound (49.6 mg, yield 89%). JH NMR (501 MHz, DMSO- ) delta ppm 8.29 (t, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.50 (dt, J = 15.1 , 8.5 Hz, 2H), 7.20 (dd, J = 10.4, 2.0 Hz, 1H), 7.11 – 6.99 (m, 2H), 6.82 (ddd, J = 9.0, 2.9, 1.1 Hz, 1H), 4.48 (s, 2H), 4.23 (d, J = 6.3 Hz, 2H), 4.03 (s, 2H), 2.13 – 1.95 (m, 4H), 1.95 – 1.77 (m, 4H); MS (ESI+) m/z 449.3 (M+H)+.

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-Chloro-3-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
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. 95-81-8, name is 2-Chloro-5-methylaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Example 1 Benzoyl chloride (21.9 g) was added dropwise to a stirred mixture of ammonium thiocyanate (13.2 g) in acetone (95 ml) and the mixture stirred for a further 20 minutes at room temperature. A solution of 6-chloro-m-toluidine (22.1 g) in acetone (30 ml) was added dropwise with stirring, the mixture stirred for a further 30 minutes at room temperature and then heated under reflux for 5 minutes. The mixture was added to water, the solid collected, dissolved in aqueous sodium hydroxide (10%; 95 ml) acidified to pH 5 with hydrochloric acid and rebasified to pH 9 with aqueous ammonia. The solid was filtered and recrystallized from toluene to give 1-(6-chloro-m-tolyl)thiourea, m.p. 152-4.

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; SCHERING AGROCHEMICALS LIMITED; EP337616; (1989); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics