Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 367-22-6, name is 4-Chloro-3-fluoroaniline, 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 367-22-6, Formula: C6H5ClFN

General procedure: A solution of the respective 1H-indazole-5-carboxylic acid or 1-alkyl-1H-indazole-5-carboxylic acid (1 or 7, 10, 1.0 mmol), 3,4-dichaloaniline or 5,6-dichloropyridin-3-amine (-5 or 6,1.1-1.2 mmol), N-ethyl-N-(3-dimethylaminopropyl)carbodiimidehydrochloride (EDC-HCl, 1.0-1.2 mmol) in methanol (5.0 mL) wasstirred over night at room temperature. The reaction was thenpoured into water (10 mL), stirred for 30 min at room temperature,filtered, washed with water (3 x 10 mL), and then dried at 70 C.The crude product was purified by column chromatography onsilica gel (mobile phase: dichloromethane/MeOH 9/1 v/v) following by recrystallization from petroleum ether/dichloromethane.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Tzvetkov, Nikolay T.; Stammler, Hans-Georg; Georgieva, Maya G.; Russo, Daniela; Faraone, Immacolata; Balacheva, Aneliya A.; Hristova, Silvia; Atanasov, Atanas G.; Milella, Luigi; Antonov, Liudmil; Gastreich, Marcus; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 404 – 422;,
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. 3460-24-0, name is 1,4-Dibromo-2-chlorobenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

1.00 g (3.02 mmol) of 1- [4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] isoquinoline,370 mg (1.37 mmol) of 1,4-dibromo-2-chlorobenzene,83.9 mg (0.0726 mmol) of tetrakis (triphenylphosphine) palladium,And 5.45 mL (5.45 mmol) of 1 M potassium carbonate aqueous solution were dissolved in 40 mL of dioxane,And the mixture was heated and stirred at 100 C. After cooling to room temperature, 400 mL of pure water was added and separation and extraction was performed with chloroform. After distilling off the solvent under reduced pressure, the obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform)2′-Chloro-4,4 “-di (1-isoquinolyl) -1,1 ‘: 4’, 1″Of a light yellow solid (Yield 490 mg, yield 68.9%).

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; TOSOH CORPORATION; FUJITA, KANA; ARAI, NOBUMICHI; NOMURA, KEISUKE; IIDA, TAKASHI; TANAKA, TSUYOSHI; (76 pag.)JP6264877; (2018); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4584-46-7, 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. 4584-46-7 name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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 round bottom flask with a stir-bar were added methyl 4-hydroxybenzoate (3.043 g, 20 mmol, 1.0 equiv.), 2-chloro-A,A-dimethylethylamine hydrochloride (3.457 g, 24 mmol, 1.2 equiv.), potassium carbonate (6.081 g, 44 mmol, 2.2 equiv.) and 30 mL isopropyl acetate. The mixture was heated at 75 C for 24 h, at which time all the methyl 4-hydroxybenzoate was consumed. Deionized water (30 mL) was then added to dissolve the potassium carbonate. The organic and aqueous phases were separated. The organic layer was washed with 30 mL water. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated and flash chromatography of the residue (gradient elution 5% methanol/EtOAc-lO% methanol/ EtOAc) gave the product, methyl 4-(2-(dimethylamino)ethoxy)benzoate (2.0 g, 45% yield), as a light yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N,N-dimethylethanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, Michael, E.; CHEN, Xiaohong; WANG, Cun-Yu; LI, Jiong; ZHENG, Jie; (167 pag.)WO2019/152536; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 870-24-6, name is 2-Chloroethanamine hydrochloride, 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 870-24-6, Quality Control of 2-Chloroethanamine hydrochloride

2-Chloroethylamine hydrochloride (E-5 A) 70% aqueous solution (1 mol) and K2CO3 (1.2 mol) were dissolved in distilled water (4 Liter). TsCl (1 mol) was added slowly with stirring. The reaction mixture was stirred at room temperature for about 24 h. The pH of the reaction mixture was adjusted to 9 by slow addition of 4 M KOH solution and the mixture kept stirring until TLC indicated all the TsCl were quenched. The resulting precipitate was collected by using suction filtration, washed with distilled water, and dried in vacuo (220 g, 95% yield), mp: 77-78 0C. 1H NMR (CDCl3): delta 2.4 (3 H, s), 3.28 (2 H, q), 3.52 (2 H, t), 5.2 ( I H, s), 7.4 (2 H, dd), 7.9 (2 H, dd).

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, 2-Chloroethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2008/63721; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 20850-43-5,Some common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, molecular formula is C8H7ClO2, 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.

50 g of 2-piperazin-1-ylpyrimidine, 60 g of triethylamine and 170 ml of isopropyl alcohol were put into a 100 ml three-necked reaction flask, and 58 g of piperonyl chloride was added dropwise with stirring at room temperature, and the mixture was dropped in 30 minutes, heated to 50 C, stirring to cool to room temperature, filtration, recovery of mother liquor, filter cake by adding 100ml water beating, pumping, plus 50ml water washing cake. Dried at 50 C, 71.5 g of piribedil crude and 99.1% by HPLC. Yield 92%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Chloromethyl)benzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; Suzhou Hongsen Pharmaceutical Co., Ltd.; Di, Jinxing; Fan, Chao; Lu, Hongbin; (6 pag.)CN106432212; (2017); A;,
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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, A new synthetic method of this compound is introduced below., COA of Formula: C7H7ClFN

Example 9 N-[(2-chloro-4-fluorophenyl)methyl]-5-oxo-1-phenyl-prolinamide (E9) 5-oxo-1-phenyl-proline (0.047 g, 0.23 mmol, prepared as described below) was dissolved in dichloromethane (~2 ml) and dimethylformamide (1 ml) and to this was added 1-hydroxybenzotriazole (0.034 g, 0.25 mmol), [(2-chloro-4-fluorophenyl)methyl]amine (0.040 g, 0.25 mmol), N-ethyl morpholine (0.032 ml, 0.25 mmol) and N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.048 g, 0.25 mmol). The mixture was stirred at room temperature for 4.5 hrs. The mixture was diluted with more dichloromethane and washed sequentially with 2M aqueous hydrogen chloride and saturated aqueous sodium hydrogen carbonate. The organic layer was filtered through a phase separator and then evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give pure N-[(2-chloro-4-fluorophenyl)methyl]-5-oxo-1-phenyl-prolinamide (0.032 g) as a white solid. LC/MS [M+H]+=347.1, retention time=2.51 minutes.

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; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 164648-75-3, A common heterocyclic compound, 164648-75-3, name is 4-Amino-3,5-dichlorobenzylamine, molecular formula is C7H8Cl2N2, 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 a suspension of Intermediate D (150 mg, 413 umol) and Intermediate A (157.8 mg, 826 umol) in CH2Cl2 (6.4 mL) was added DIPEA (143 uL, 821 umol). The mixture was stirred at rt overnight. Solvents were removed in vacuo. The residue was loaded onto a silica gel chromatography column, and eluted with a 0 to 75% EtOAc/hexane gradient to afford the pure product (181.8 mg, 87% yield). LC-MS (M+H)+=506. LC-MS RT (column 1)=2.806/4.00. 1H NMR (500 MHz, CD3OD, rotamers seen): 67.23-7.15 (m, 3.3H), 7.14-7.08 (m, 0.7H), 6.73 (t, J=7.3 Hz, 0.7H), 6.63-6.55 (m, 1.7H), 6.49 (d, J=7.9 Hz, 0.6H), 4.42-4.30 (m, 2H), 4.19-4.14 (dd, J=2.4, 8.9 Hz, 0.3H), 4.11-4.06 (dd, J=2.4, 9.5 Hz, 0.7 Hz), 3.86-3.80 (m, 0.7H), 3.56-3.48 (m, 0.3H), 3.31-3.24 (m, 1H), 2.41-2.28 (m, 1H), 2.22-2.14 (m, 1H), 2.11-2.03 (m, 2H), 1.47 (s, 2.7H), 1.34 (s, 6.3H). 13C NMR (500 MHz, CD3OD, rotamers seen): delta 177.56, 163.08, 155.35, 147.07, 140.60, 129.23, 128.94, 127.74, 127.60, 127.53, 119.27, 118.03, 115.86, 112.90, 112.11, 83.69, 79.56, 78.45, 65.96, 64.55, 49.16, 43.28, 43.15, 31.56, 31.47, 27.44, 27.21, 24.01, 23.91.

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; Bristol-Myers Squibb Company; US2007/232679; (2007); 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

4-Trifluoromethyl-6-(3-fluoro-5-chloro)phenyl-2(1H)-quinolinone (Compound 732, Structure 145 of Scheme XXX, Where R=H, R1=Trifluoromethyl, R2=3-Fluoro-5-chloro) 3-Chloro-5-fluorobenzeneboronic Acid (Compound 733, Structure 144 of Scheme XXX, Where R2=3-Fluoro-5-chloro): This compound was prepared according to General Procedure XXIII in Example 406 from 1-bromo-3-chloro-5-fluorobenzene (20 g, 0.18 mmol), n-BuLi (8.2 M in hexane, 21 mL, 0.18 mmol), and trimethyl borate (60 mL, 0.53 mmol) to give 2,3-difluoro-benzeneboronic acid as a white solid.

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; Ligand Pharmaceuticals Incorporated; US6566372; (2003); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1871-57-4, These common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 a solution of Compound 1 (1.32 g, 10.5 mmol) in DMF (20 mL) was added NaH (960 mg, 24 mmol) at 0 C., the mixture was stirred at 0 C. for 30 min. Then compound 2 (1.61 g, 10 mmol) was added at 0 C. The mixture was stirred at 15 C. for 2 hours. TLC showed that starting material was consumed completely. Saturated NH4Cl (100 mL) was added to quench the reaction. The solvent was removed in vacuo and the residue was extracted with EA (100 mL*2). The organic layer was concentrated and purified by silica gel column (PE:EA=4:1) to give compound 3 (1.1 g, yield: 51%) as colorless oil. 1H NMR (400 MHz, CDCl3): delta: 5.12-4.91 (m, 2H), 4.29-4.03 (m, 4H), 3.76-3.45 (m, 4H), 1.47 (s, 9H).

Statistics shows that 3-Chloro-2-chloromethyl-1-propene is playing an increasingly important role. we look forward to future research findings about 1871-57-4.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); 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. 4152-90-3, name is (3-Chlorophenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 4152-90-3

A solution of 5-chloro-jV-cyclohexylpyrazolo[ 1 ,5-alpha]pyrimidine-3-carboxamide(28 mg, 0.09 rnM, 1.0 equiv), 3-chlorobenzylamine (28 mg, 0.18 rnM, 2.0 equiv), N5N- diisopropylethylamine (26 mg, 0.18 rnM, 2.0 equiv) and 2 rnL of ethanol were microwaved at 120 0C for 10 minutes. TLC (95:5 dichloromethane methanol) showed reaction complete. The reaction mixture was cooled, the crystalline product collected by filtration, washed with cold ethanol and air dried to yield 29.7 mg (77percent) of 5-(3-chlorobenzylamino)-7V- cyclohexylpyrazolo[l,5-alpha]pyrimidine-3-carboxamide. LCMS (ESI) m+H = 384.2; 1H NMR (400 MHz, OMSO-d) delta: 8.61 (overlapping d and t, 2 H), 8.06 (s, 1 H), 7.60 (d, 1 H), 7.4- 7.25 (m, 4 H), 6.49 (d, 1 H), 3.70 (m, 1 H), 1.75-1.5 (m, 5 H), 1.4-0.8 (m, 5 H).

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; GENENTECH, INC.; BLANEY, Jeffrey; GIBBONS, Paul A.; HANAN, Emily; LYSSIKATOS, Joseph P.; MAGNUSON, Steven R.; PASTOR, Richard; RAWSON, Thomas E.; ZHOU, Aihe; ZHU, Bing-Yan; WO2010/51549; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics