Tag: M.W=100-200

Synthetic Route of 72235-56-4, 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. 72235-56-4 name is 3-Chloro-4-fluorobenzylamine, 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 mixture of 8-(benzyloxy)-2-methyl-1-oxo-1, 2,3, 4-tetrahydro-pyrrolo [1, 2-a] – pyrazine-7-carboxylic acid (200 mg, 0.67 mmol), 3-chloro-4-fluorobenzylamine (0. 16 g, 1.00 mol), and benzotriazol-l-yloxy-tris (dimethylamino) phosphonium hexafluorophophate (BOP, 0.35 g, 0.79 mmol) in anhydrous dichloromethane (10 mL), diisopropylethylamine (0.17 g, 1.33 mmol) was added. The resultant solution was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum, and the residue partitioned between dichloromethane and aq HC1. The organic extract was washed with aq sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the titled amide. 1H NMR (400 MHz, CDC13) 8 7.47 (br d, J = 7.5 Hz, 2H), 7. 32-7 18 (m), 7.01 (br d, 2H), 5.35 (s, 2H), 4.33 (d, J = 6.1 Hz, 2H), 4.14 (q, J = 5.7 Hz, 2H), 3.67 (t, J = 5.7 Hz, 2H), 3.14 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-fluorobenzylamine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2005/41664; (2005); A1;,
Chloride – Wikipedia,
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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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, A new synthetic method of this compound is introduced below., name: 1-(2-Chloroethyl)azepane hydrochloride

Add sodium hydride (324 mg, 8.0 mmol) into a solution of 4- [6-benzyloxy-2- (4- fluoro-phenyl)-naphthalen-1-yloxy]-phenol (1.18 g, 2.7 mmol) in DMF (10 mL) and stir for 20 minutes at room temperature. Add 2- (hexamethyyleneimino) ethyl chloride hydrogen chloride (1.07 g, 5.4 mmol) and stir at room temperature for 12 hours. Add H20 (10 mL) and diethyl ether (100 mL). Separate layers and wash the aqueous layer with diethyl ether (2 x 50 mL). Combine organic layers, dry with magnesium sulfate and concentrate in vacuo. Purify the residue over silica gel, eluting the material with a step gradient of methanol/dichloromethane (0percent to 10percent), to obtain 1.0 g of the title compound (66percent): mass spectrum (ion spray) m/z=562.3 (M+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; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
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Electric Literature of 2613-32-3,Some common heterocyclic compound, 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, molecular formula is C6H4ClF2N, 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 100 mg (0.28 mmol) trans-4-({[4-(phenoxycarbonyl)-1H-imidazol-5-yl]carbonyl}amino)cyclohexane-carboxylic acid in 5 ml dichloromethane 62 p1(0.45 mmol) 1-chloro-N,N,2-trimethylprop-1-en-1-amine were added and the mixture was stirred at roomtemperature for 30 minutes. 68 p1(0.84 mmol) pyridine and 31 p1(0.28 mmol) 2-chloro-4,5-difluoroaniline were added and the reaction was stirred at room temperature for 30 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4,5-difluoroaniline, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Synthetic Route of 14752-66-0, 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. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Azoles 1 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and NBS (0.5 mmol) were dissolved in 2 mL of 1,4-dioxane solvent. the reaction mixture was stirred at room temperature under air for 12 h. After the reaction, the resulting mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and the solvent was then removed under vacuum. The residue was purified by flash column chromatography on silica gel (petroleumether/ethyl acetate, 3:1) to afford the corresponding product.

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

Reference:
Article; Fu, Lili; Bao, Xiaodong; Li, Shanshan; Wang, Lingtian; Liu, Zhiguo; Chen, Wanzhi; Xia, Qinqin; Liang, Guang; Tetrahedron; vol. 73; 17; (2017); p. 2504 – 2511;,
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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 2268-05-5 as follows. Formula: C6H3Cl2F

A mixture of 4-chloro-1H-pyrazolo[4,3-c]pyridine (150 mg, 0.990mmol), 1,6-dichloro-2-fluorobenzene (300mg, 1.80mmol) andpotassium carbonate(450 mg, 3.26mmol) in dry DMF(3.0 mL)was heated at 85 C for 20 h.The reaction was quenched with water (30 mL) and extracted withethyl acetate (3 x 20 mL).The combined organic extracts were washed with brine, dried over Na2SO4andconcentrated under reduced pressure.The residue was purified on silica gel(ethylacetate :petroleum ether = 1 : 10)to givethe desired productas a white solid(10 mg, 3.5% yield)anditsregio-isomeras awhitesolid(30 mg, 11% yield).4-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine:1H-NMR(CDCl3):delta8.31 (d,J= 0.5 Hz,1H), 8.13 (d,J= 6.0 Hz,1H), 7.64-7.56(m, 3H), 7.49 (m, 1H).LCMS(ESI) m/z: 298.0[M+H+].4-Chloro-1-(2,6-dichlorophenyl)-1H-pyrazolo[4,3-c]pyridine,1H-NMR(CDCl3):delta8.44(d,J= 0.5 Hz,1H), 8.24(d,J= 6.0 Hz,1H), 7.57 -7.47(m, 3H), 7.00(d,J= 6.0 Hz,1H).LCMS(ESI) m/z: 298.0[M+H+].

According to the analysis of related databases, 2268-05-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 13334-71-9, name is 4-Chloro-3-methylanisole, molecular formula is C8H9ClO, 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: C8H9ClO

A solution of 4-chloro-3-methylanisole (3.0 g, 19.2 mmol) (Acros) and potassium permanganate (7.57 g, 47.9 mmol) in water (60 ML) was heated at reflux for 4 h.The precipitate was filtered and the solution was extracted with EtOAc. The aqueous phase was acidified with conc. HCl. The precipitate was collected by filtration, washed with water and dried to give the product. (Yield 0.78 g, 22%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13334-71-9, its application will become more common.

Reference:
Patent; Chen, Jian Jeffrey; Luk, Kin-Chun Thomas; US2004/97493; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1716-42-3, name is 1-(3-Chloropropoxy)-4-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 1716-42-3, COA of Formula: C9H10ClFO

EXAMPLE 17 4-[Bis(4-fluorophenyl)methyl]-1-[3-(4-fluorophenoxy)propyl]piperidine Following the combined procedures of Examples 14 and 16, 4-[bis(4-fluorophenyl)methyl]piperidine and 4-(3-chloropropoxy)-1-fluorobenzene were reacted and worked up by chromatography in Example 16, to give the free base in 53percent yield as a yellow oil after drying in vacuo at 80° C. overnight. Analysis: Calculated for C27 H28 NOF3: C, 73.78; H, 6.42; N, 3.19. Found: C, 73.64; H, 6.39; N, 3.14.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Chloropropoxy)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; A. H. Robins Company, Incorporated; US4810713; (1989); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, molecular formula is C7H8ClNO, 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. Computed Properties of C7H8ClNO

1.45g of 4-chloro-2-methoxyaniline was dissolved in a solution of 60 ml of water and 10 ml of concentrated sulfuric acid and cooled to below 5 C in an ice bath. Further, 634 mg of sodium nitrite was dissolved in 1 ml of water and slowly added dropwise to the reaction solution, and the mixture was stirred under ice cooling for 45 minutes, and then 1.98 g of potassium iodide aqueous solution (5 ml) was added dropwise. After stirred at room temperature for 1 hour, the mixture was extracted with EtOAc, washed with a saturated aqueous solution of sodium thiosulfate, dried over anhydrous sodium sulfate and then isolated by column chromatography (PE 100%) to obtain 2.17 g of liquid, yield 88%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93-50-5, its application will become more common.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; DUAN, Wenhu; GENG, Meiyu; WANG, Yuming; AI, Jing; FAN, Jun; DAI, Yang; DING, Jian; (133 pag.)EP3486244; (2019); A1;,
Chloride – Wikipedia,
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Reference of 918538-05-3,Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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; 2-(4-(3-Cyclopropyl-l/f-pyrazol-5-ylamino)pyrrolo[l,2-fJ[l,2,4]triazin-2-yl)- lambda-(6-fluoropyridin-3-yl)pyrazolidine- 1 -carboxamide IA. 2-Chloro-N-(3 -cyclopropyl- lH-pyrazol-5-yl)pyrrolo [ 1 ,2-f] [ 1 ,2,4]triazin-4- amine [00146] A mixture of 2,4-dichloropyrrolo[l,2-f][l,2,4]triazine (977 mg, 5.2 mmole), S-cyclopropyl-lH-pyrazoW -amine (640 mg, 1 equiv), and diisopropylethylamine (1.54 mL, 1.7 equiv) in isopropyl alcohol (5 mL) was stirred at room temperature overnight. The product was collected by filtration (1.18 gm, 83% yield): MS: 275 (M+eta)~; HPLC Ret Time: 1.56 min. (Phenomenex-Luna s 10 3.0 x 50 mm column, 3 min gradient, 4 mL/min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/111531; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: 3,4-Dichlorobenzylamine

Methyl 6-(3,4-dichlorobenzylamino)nicotinate A mixture of (3,4-dichlorophenyl)methanamine (1.010 mL, 7.58 mmol), TEA (1.218 mL, 8.74 mmol), and methyl 6-chloronicotinate (1 g, 5.83 mmol) in ethanol (29 mL) was heated at 120° C. for 5 min in a microwave oven. The reaction mixture was further heated at 100° C. for 54 h, then concentrated. The residue was purified by flash chromatography on silica gel using 5-35percent ethyl acetate in hexanes. The desired fractions were concentrated to give methyl 6-(3,4-dichlorobenzylamino)nicotinate as a pale yellow solid (0.55 g, 33percent). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.77 (1H, s), 8.01 (1H, dd, J=8.78, 2.01 Hz), 7.33-7.52 (2H, m), 7.19 (1H, d, J=8.03 Hz), 6.37 (1H, d, J=8.78 Hz), 5.37 (1H, br. s.), 4.58 (2H, d, J=6.02 Hz), 3.88 (3H, s). LCMS: R.T.=2.81; [M+H]+=311.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102-49-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics