Tag: M.W=100-200

Reference of 2106-04-9, 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. 2106-04-9 name is 3-Chloro-2-fluoroaniline, 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.

General procedure: To a solution of (E)-N-(2-cyano-4-nitrophenyl)-N,N-dimethylformimidamide 17 (6.0 g, 2.7 mmol) and acetic acid (45 mL) was added 3-fluoroaniline (18a, 3.3 g, 3.0 mmol) at room temperature. The reaction mixture was heated up to reflux temperature for 1 h. After completion of the reaction, the resulting mixture was cooled to room temperature. The solid separated was filtered and washed with ether to give 19a, 6.5 g (83%);

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

Reference:
Article; Marvania, Bhavin; Lee, Pei-Chih; Chaniyara, Ravi; Dong, Huajin; Suman, Sharda; Kakadiya, Rajesh; Chou, Ting-Chao; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long; Bioorganic and Medicinal Chemistry; vol. 19; 6; (2011); p. 1987 – 1998;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6781-98-2, name is 2-Chloro-1,3-dimethylbenzene, molecular formula is C8H9Cl, 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 6781-98-2

General procedure: To a 50 mL Schlenk tube containing base (1.5 mmol) and precatalyst 4a (1 mol %, 0.0083 g) purged with N2 (three times), amine (1.2 mmol) was added via syringe, and the resulted mixture was allowed to stir at room temperature for 2-3 min. Solvent (1 mL) was then injected via syringe followed by the aryl chloride (1.0 mmol). If the aryl chloride was a solid, it was introduced into the vial prior to purging with N2. At this time, the reaction was stirred for 24 h at 100 C. After cooling to the room temperature, the reaction mixture was concentrated in vacuo and directly purified via silica gel flash chromatography. N-(2,6-Dimethylphenyl)-2,4,6-trimethylaniline (26) ;1H NMR (CDCl3, 400 MHz, 298 K): delta=6.97 (d, J=7.6 Hz, 2H), 6.81-6.78 (m, 3H), 4.71 (br s, 1H), 2.25 (s, 3H), 1.99-1.95 (m, 12H); 13C NMR (CDCl3, 100 MHz, 298 K): delta=142.14, 138.94, 131.43, 130.40, 129.17, 128.74, 128.34, 120.91, 20.55, 19.06, 18.96; GC-MS: tR=16.270 min, m/z=239.1 [M]+, 239.1, 222.1, 208.1, 132.0, 120.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6781-98-2, its application will become more common.

Reference:
Article; Fang, Weiwei; Jiang, Jian; Xu, Yong; Zhou, Juefei; Tu, Tao; Tetrahedron; vol. 69; 2; (2013); p. 673 – 679;,
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Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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. Safety of 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide

General procedure: Ph(But)P(O)Cl or 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (5.0mmol) was added to the suspension of NaH (0.133g, 5.5mmol) in THF (25mL). Subsequently, 5,7-dibromo-2-methylquinolin-8-ol (1a), 5-fluoro-2-methylquinolin-8-ol (1i) (5.0mmol) in THF (5mL), was added. The reaction was carried out for 24 h under reflux. The mixture was allowed to cool to room temperature. The reaction was neutralized with aqueous solution of KHSO4. After extraction with CH2Cl2 (3¡Á50mL), the organic phase was dried over MgSO4, followed by filtration and solvent evaporation. The crude product was purified by chromatography and crystallization.

The synthetic route of 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nycz, Jacek E.; Szala, Marcin; Malecki, Grzegorz J.; Nowak, Maria; Kusz, Joachim; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 351 – 359;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine 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 4584-46-7, Product Details of 4584-46-7

To a solution of 4-hydroxy-3-methoxybenzaldehyde (10g) in DMF (500ml) were added potassium carbonate (18.20g)and 2-chloro-N,N-dimethylethylamine hydrochloride (14.08g). The reaction mixture was stirred at 80C for 1 h30min. The suspension was filtrated off and the filtrate was diluted with Et20 and sat. aq. NaCI. The aq. layer was extracted with Et20, the combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 70g cartridge, solvent A: DCM, solvent B: MeOH, gradient in %B: 2 to 4, flow rate: 20ml/min) to afford 7.3g of a yellow oil. LC-MS (A): tR = 0.60min; [M+H]+: 224.48.

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; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GRISOSTOMI, Corinna; KIMMERLIN, Thierry; REMEN, Lubos; SIENDT, Herve; VERCAUTEREN, Magali; WELFORD, Richard; (138 pag.)WO2016/177690; (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 1303587-99-6 as follows. Safety of 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine

Synthesis of2-chloro-8-(4-(trifluoromethoxy) benzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0456] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (5 mL) under argon atmosphere were added sodium hydride (42 mg, 1.75 mmol) and l-(bromomethyl)-4-(trifluoromethoxy) benzene (268 mg, 1.05 mmol) at 0C. The reaction mixture was warmed to RT and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 40% EtOAc:hexane to afford 2-chloro-8-(4- (trifluoromethoxy) benzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (160 mg, 53%>) as an off-white solid. 1H-NMR (DMSO-<, 400 MHz): delta 7.71 (s, 1H), 7.42 (d, 2H), 7.34 (d, 2H), 4.80 (s, 2H), 4.21-4.19 (m, 2H), 3.52-3.50 (m, 2H); LCMS: 345.8 (M+); (column; X- Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.94 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc/hexane (R 0.6). According to the analysis of related databases, 1303587-99-6, the application of this compound in the production field has become more and more popular. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 106131-61-7,Some common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, molecular formula is C2Cl2N4, 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 3,6-dichloro-1,2,4,5-tetrazine (500 mg, 3.31 mmol) in Tol. (5 mL) was added 2-methylbut-3-yn-2-ol at 20 C. The mixture was stirred at 115 C. for 16 hours under sealed tube. LCMS showed desired MS. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 4:1, TLC) to give 33a. MS mass calculated for [M+1]+ (C7HCl2N2O) required m/z 207.0, LCMS found m/z 207.0; 1H NMR (400 MHz, CDCl3) delta 7.98 (s, 1H) 2.17 (s, 1H) 1.77 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dichloro-1,2,4,5-tetrazine, its application will become more common.

Reference:
Patent; Terns, Inc.; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; ROMERO, F. Anthony; US2020/62742; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9,Some common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5-1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120-130 C until the aniline was fully consumed (3-14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1-2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wimmer, Laurin; Parmentier, Michael; Riss, Bernard; Kapferer, Tobias; Ye, Chao; Li, Lei; Kim, Hongyong; Li, Jialiang; Synthesis; vol. 50; 10; (2018); p. 2027 – 2032;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

The chemical industry reduces the impact on the environment during synthesis 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4152-90-3, 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 4152-90-3 as follows.

A solution of tert-butyl (trans)-2-(6-bromopyridin-3-yl)cyclopropylcarbamate (Intermediate E, 350 mg, 1.118 mmol), 3-chlorobenzylamine (237 mg, 1.677 mmol), Sodium tert-butoxide (161 mg, 1.677 mmol) in 1,4-dioxane (7 mL) was degassed for 30 min, tris(dibenzylidene acetone)dipalladium(0) (51 mg, 0.055 mmol), 4,5-Bis(diphenyl phosphino)-9,0-dimethyl xanthene (193 mg, 0.335 mmol) was added and heated for 4 h at 80¡ã C. After completion, the solvent was removed, the residue was poured into ice cold water (10 mL) and extracted with EtOAc (2*20 mL). The combined extracts were washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography to give tert-butyl (trans)-2-(6-(3-chlorobenzylamino) pyridin-3-yl)cyclopropyl carbamate (100 mg, yield: 24percent) as white solid.

According to the analysis of related databases, 4152-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laria, Julio Castro-Palomino; Fyfe, Matthew Colin Thor; Pedemonte, Marc Murtinell; Munoz, Alberto Ortega; Valls Vidal, Nurla; US2013/289076; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2106-02-7, 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.

Example 99 i-^-Chloro^-fluorophenylJ^-^-chloro^-fluorophenylJmethyl^S- piperazinedione (E99)Methyl [[(2-chloro-4-fluorophenyl)methyl](2-oxoethyl)amino](oxo)acetate (0.29 g, 1.0 mmol, prepared as described earlier) and 2-chloro-4-fluoraniline (0.29 g, 2.0 mmol) were dissolved in 2% acetic acid/methanol (10ml) at room temperature. The mixture was stirred for 15 minutes before polymer-supported cyanoborohydride (0.98 g, 4.0 mmol) was added. The mixture was stirred at room temperature overnight, then filtered through an SCX cartridge (Varian, 5g) and the filtrate concentrated in vacuo. The residue was then dissolved in 1-butanol (1.5 ml) and heated to 200 0C by microwave irradiation for 1 hour. The mixture was concentrated in vacuo and purified by mass-directed automated HPLC to yield 1-(2-chloro-4-fluorophenyl)-4-[(2-chloro- 4-fluorophenyl)methyl]-2,3-piperazinedione (0.161 g). LC/MS [M+H]+ = 385, retention time = 2.78 min.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; CHAMBERS, Laura Jane; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; STEADMAN, Jon Graham Anthony; WALTER, Daryl Simon; WO2010/125103; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics