Tag: M.W=100-200

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. 1207625-18-0, name is 3-Chloro-7H-pyrrolo[2,3-c]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H4ClN3

General procedure: To a 15 mL round-bottomed flask were added a stir bar, 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (51 mg, 0.20 mmol), 4-trifluoromethylbenzyl bromide (52 mg, 0.22 mmol), powdered KOH (42 mg, 0.75 mmol) and DMSO (2.0 mL). The resultant mixture was stirred at room temperature for 22.5 hours before diluting with 100 mL EtOAc and washing with water (¡Á3). The organic layer was isolated, dried, filtered, and concentrated to dryness. The crude product was subjected to FCC to give the title compound as a pale-yellow solid (54 mg, 66%). The title compound was prepared in a manner similar to that described in Example 1 using (4-cyclobutyl-2-fluoro-3-methoxyphenyl)boronic acid and 3-chloro-7H-pyrrolo[2,3-c]pyridazine. MS (ESI): mass calcd. for C17H16FN3O, 297.13; m/z found, 298.1 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 12.05 (s, 1H), 8.15 (d, J=2.2, 1H), 7.80 (d, J=3.4, 1H), 7.71 (m, 1H), 7.21 (d, J=8.1, 1H), 6.61 (d, J=3.4, 1H), 3.94 (d, J=1.2, 3H), 2.44-2.35 (m, 2H), 2.25-2.14 (m, 2H), 2.13-2.05 (m, 1H), 1.81 (d, J=7.1, 2H).

According to the analysis of related databases, 1207625-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-05-0, 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 2106-05-0 as follows.

4-Bromo-5-chloro-2-fluoroaniline To a mixture of 5-chloro-2-fluoroaniline (1 equiv.) in acetonitrile (0.5 M) was added N-bromosuccinimide (1 equiv.) at 25 C. The mixture was stirred at 25 C. for 1 h. The mixture was concentrated to a residue, the residue was purified via silica gel chromatography to give 4-bromo-5-chloro-2-fluoroaniline (91%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta ppm: 7.23 (d, J=10.2 Hz, 1H), 6.88 (d, J=8.4 Hz, 1H), 3.92-2.64 (br, 2H).

According to the analysis of related databases, 2106-05-0, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-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 4863-91-6, Application In Synthesis of 3-Chloro-5-fluoroaniline

To a solution of compound 37.3 (1 eq) in toluene (37 eq) cooled in an ice water bath was added N,N,N’,N’-te¡êramethylethylenediamine (3 eq) and chlorotrimethylsilane (4 eq) the reaction mixture was allowed to come to rt for 30 min. Iodine (1.2 eq) was added portion wise at 10 C. After the addition of iodine was complete the reaction mixture stirred at RT for 3 h followed by diluting with EtOAc and washing with aq a2S204, dried over Na2SC>4 and concentrated in vacuo to afford a residue. To a solution of 3-chloro-5-fluoroaniline (2 eq) in THF (40 eq) was added sodium hydride (60% oil dispersion in mineral oil 3 eq) and stirred at RT for 15 min. Added a solution of the above residue in THF (10 mL) and stirred at RT for 2 h followed by diluting with EtOAc and washing with 5% citric acid, dried over Na2SC>4 and the solvent removed in vacuo. The residue was purified by flash chromatography (10% EtOAc/Hexane to 100% EtOAc) to povide compound 37.4 (48% yield) as a white foam. EIMS (m/z): calcd. for C21H28CIF2N3O3 (M++Na) 466.92, found 466.00.

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:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 75717-77-0, 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. 75717-77-0 name is 2,4-Dichlorophenylacetylene, 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.

Weighed 2,4-dichlorobenzyl alkyne compound (81.6mg, 0.5mmol) into the round bottom flask; re-weighed compound 3,4-methylenedioxy-benzyl azide (120mg, 0.68mmol, 1.4eq) into round-bottomed flask; dimethyl sulfoxide (0.2mL); amount of tert-butanol solution (4mL) and H2O (2mL) dropped to the mixture; after five co-catalyst weighed water copper sulfate (390mg); and then said take ascorbic acid sodium salt (290mg). The clarification becomes cloudy, yellow. Was stirred for 5 hours at room temperature, after treatment experiment, ice-water was added with stirring (15mL), the reaction was quenched; (30mL ¡Á 3) and extracted with ethyl acetate; the organic phase was washed with H2O (25mL ¡Á 2), saturated chloride sodium solution (30mL ¡Á 2) and washed; with an appropriate amount, and the organic phase was dried over anhydrous sodium sulfate; filtered andAnd concentrated to a solid, brown, purified by column chromatography [the V (dichloromethane) :V (petroleum ether) = 1: 1] to give a white solid 125.0 mg,Yield 75%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichlorophenylacetylene, and friends who are interested can also refer to it.

Reference:
Patent; Changzhou University; Chen, Xi; Liang, Cuirong; Yang, Qinghong; Ren, Jie; Jin, Guihua; Huang, Qianhui; Xu, Yuanyuan; Hu, Kun; (32 pag.)CN105440020; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. Product Details of 918538-05-3

69A. Preparation of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine A solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with 3-cyclopropyl-1H-pyrazol-5-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOH and dried under vacuum to afford 69A as a solid (1.3 g, 90%). HPLC tR=3.301 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+=275.37. A solution of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine (1A) (100 mg, 0.36 mmol) and piperidine-4-carboxamide (467 mg, 3.6 mmol) in NMP (1 mL) was heated in a microwave safe tube (CEM Corporation, 10 mL) at 100 C. for 40 minutes using 300 W continuous power. The reaction was diluted with EtOAc (10 mL) and washed with 10% aqueous LiCl solution (2*10 mL). The organic layers were combined and dried (Na2SO4), filtered and concentrated. The crude product was purified by preparative reversed-phase HPLC to afford the title compound (23 mg, 15%). HPLC tR=2.398 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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 1: Preparation of Intermediate 3,5-chlorophenyl)hydrazine (I-la) To a cold suspension of 3, 5-dichloroaniline (15.0 g, 92.58 mmol, x 4 batches) in conc. HCI (45 mL, for each batch) was added a solution of NaNO2 (7 g, 101 .44 mmol, for each batch) in water (65 mL, for each batch) at 100C and stirred for 30 minutes. Then a solution of SnCI2 (52.49 g, 277.7 mmol, for each batch) in conc. HCI (45 mL, foreach batch) was added slowly. After addition was complete, a white precipitate was formed which was stored at 4C for 7 h. The precipitated solid was collected by filtration, washed with hexane and suspended in 10% aq NaOH solution (pH = 13) and extracted with Ethyl acetate (4 x 200 mL). The organic layer was washed with water (250 mL), brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Thesolids thus obtained from 4 batches were combined and was washed with n-hexane to afford 45 g (68.6%) of 3,5-chlorophenyl)hydrazine a-ia) as an off-white solid.NMR (400 MHz, DMSO-d6): 66.75 (5, 1 H), 6.72 (5, 2H), 5.30 (br s, 1 H, -NH), 3.58 (br s, 2H, -NH2). ESI MS: m/z 179.0 (M+2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; KONDREDDI, Ravinder Reddy; SMITH, Paul William; WO2014/37900; (2014); 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. 1005-56-7, name is O-Phenyl carbonochloridothioate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of O-Phenyl carbonochloridothioate

The pyridine (2.01 mL, 25.03 mmol) andphenyl chlorothionoformate(5.18 mL, 37.52 mmol) were added in the compound 3 (5.0 g, 12.50 mmol) in 50 mL CH2Cl2. The mixture was stirred at room temperature for 3 h. The solution was washed with brine and dried by anhydrous MgSO4. After concentration, the residue was purified by flash chromatography on silica gel (hexane/EtOAc, 4/1) to give thiocarbonate compound (4) (5.23 g, 78)

According to the analysis of related databases, 1005-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WENG, Ching-Feng; CHEN, Chin-piao; SHIVAJI, Sulake Rohidas; HUANG, Zi-Ling; (74 pag.)WO2016/37566; (2016); 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. 33786-89-9, name is 5-Chloro-m-phenylenediamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H7ClN2

General procedure: A solution of di-tert-butyl-dicarbonate (6.484g, 29.7 mmol) in dry THF (35 mL) was added over a period of 30 min to asolution of 5-isopropylbenzene-1,3-diamine (4.462 g, 29.7 mmol) in dry THF (35mL). The mixture was allowed to stir for 22 h, and the solvent was removedusing a rotary evaporator. The residue was purified by flash columnchromatography on silica gel to give compound 11n as a dark red solid(4.135 g, 56 %).

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 33786-89-9.

Reference:
Article; Yu, Lei; Huang, Minhao; Xu, Tianfeng; Tong, Linjiang; Yan, Xiao-e; Zhang, Zhang; Xu, Yong; Yun, Caihong; Xie, Hua; Ding, Ke; Lu, Xiaoyun; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1107 – 1117;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2729-34-2, name is 3,5-Dichloro-4-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 2729-34-2, Product Details of 2729-34-2

3,5-dichloro-4-fluoroaniline (1534 mg, 8.5 mmol) dissolved in toluene (10 mL) was added to 4-chlorosulfonyl-1-methyl-pyrrole-2-carbonyl chloride (2063 mg, 8.52 mmol) in toluene (115mL) at reflux and refluxed 2 hours. The reaction mixture was filtered while still hot and thefiltrate was concentrated , yielding crude 5- [(3,5 -dichloro-4-fluorophenyl)carbamoyl] -1-methyl-pyrrole-3-sulfonyl chloride as a crude beige powder which was used as such.?H NMR (400MHz, acetonitrile-d3) oe ppm 3.96 (s, 3 H), 7.39 (d, J=2.0 Hz, 1 H), 7.71 – 7.77 (m, 3 H), 8.78 (br.s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloro-4-fluoroaniline, and friends who are interested can also refer to it.

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

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. category: chlorides-buliding-blocks

Step 2. Synthesis of 3-(benzo[d][1 ,3]dioxol-5-ylmethyl)-5-(3-nitrobenzylidene)imidazo- lidine-2,4-dione; DBU (3.82 mmol, 0.961 g) is added into solution of 5-(3-nitrobenzylidene)imidazolidine-2,4- dione (3.19 mmol, 0.743 g) at O’O and the solution left to warm to room temperature. 5- (Chloromethyl)benzo[d][1 ,3]dioxole (6.37 mmol, 2.174 g, 50% soln in CH2CI2) is added and the reaction mixture stirred for 3 hours. Subsequently 0.5 M HCL solution is added and extracted with ethylacetate (2 x 50 ml_) dried over MgSO4 and the solvent removed under reduced pressure. The obtained product is recrystallized from diisopropylether to afford 0.13 (1 1%) of 3-(benzo[d][1 ,3]dioxol-5-ylmethyl)-5-(3-nitrobenzylidene)imidazo-lidine-2,4-dione.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20850-43-5, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICAL D.D.; WO2008/43733; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics