Tag: M.W=100-200

Application of 6940-78-9,Some common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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.

(b) Under a nitrogen atmosphere, 81.6 g (0.5 mol) of 7-hydroxy-1H-quinolin-2-one, 103 g (0.6 mol, 1.2 ep) of bromochlorobutane, and 103.5 g of potassium carbonate were added to the flask. Mol, 1.5 ep), 816 mL of acetone, stirred and heated at 60 C., and reacted for 8 hours.After the reaction is completed, cool down to 20C, filter, concentrate the filtrate to recover some acetone, and add water to the remaining residue.Solids were formed, stirred for 1 hour, filtered off with suction, washed with water, sucked dry, and dried in vacuum to obtain a crude product of compound (III) to obtain 110 g of compound (III) in a yield of 86%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-chlorobutane, its application will become more common.

Reference:
Patent; Zhejiang Liaoyuan Pharmaceutical Co., Ltd.; Song Zhigang; Yang Minhua; Cui Jianfeng; Chen Weijun; (16 pag.)CN106831739; (2017); A;,
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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. 4152-90-3, name is (3-Chlorophenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4152-90-3

General procedure: 10495] In an oven-dried vial, G8 (1 equiv.) and benzotriazol-1 -yloxytripyrrolidinophosphonium hexafluorophosphate (1.2 equiv.) were dissolved in dichloromethane (0.1 M). Diisopropylethylamine (1 equiv.) was added, and the reaction was stirred at room temperature for 1-2 hours. Afier complete complexation by TLC, amine (1-3 equiv.) and additional diisopropylethylamine (1-3 equiv.) were added, and the reaction was allowed to stir at room temperature for 12-16 hours. The reaction was concentrated and purified by flash silica chromatography (hexanes/ethyl acetate) to provide the amide. (Note: G16a can be isolated and purified prior to the addition of amine.) Yield: 130.0 mg, 91percent.10502] ?H NMR (CD3OD, 500 MHz): oe 7.35 (t, J=1 .8 Hz,1H), 7.33-7.22 (m, 4H), 5.78 (dt, J=5.5, 2.0 Hz, 1H), 5.05 (t,J=2.5 Hz, 1H), 4.91 (t, J=1.9 Hz, 1H), 4.70 (t, J=5.3 Hz, 1H),4.38 (d, J=15.0 Hz, 1H), 4.34 (d, J=15.0 Hz, 1H), 4.19 (d,J=5.3 Hz, 1H), 3.38-3.33 (m, 1H), 2.68 (d, J=6.0 Hz, 1H),2.49 (dt, J=16.3, 3.0 Hz, 1H), 2.38 (d, J=6.0 Hz, 1H), 2.16(ddt, J=16.0, 2.0, 1.0 Hz, 1H), 2.02-1.88 (m, 1H), 1.76-1.62(m, 2H), 1.51-1.46 (m, 1H) 1.46 (dd, J=11.0, 3.0 Hz, 1H),1.36 (dd, J=1 1.0,2.5Hz, 1H), 1.15 (s, 3H). HRMS(ESI): mlzcalc. for C25H29NO5Cl[M+H]: 470.1734. found: 470.1740.10500] G1 6b: Prepared from 3-chlorobenzylamine.

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Board of Trustees of the University of Illinois; Hergenrother, Paul J.; Huigens, III, Robert W.; Morrison, Karen C.; Hicklin, II, Robert W.; Flood, JR., Timothy A.; US2015/274638; (2015); A1;,
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Electric Literature of 932-96-7, 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 932-96-7 as follows.

(a) 4-r(4-Chlorophenyl)(methyl)aminolbenzaldehvde; Toluene (100 mL) and 4-chloro-Lambda/-methylaniline (4.58 mL, 37.8 mmol) were added to a mixture of Cs2CO3 (17.26 g, 53 mmol), Pd(OAc)2 (0.42 g, 1.9 mmol), BINAP (1.77 g, 2.8 mmol) and 4-bromobenzaldehyde (7 g, 37.8 mmol). The mixture was stirred at 85 0C for 20 h and filtered through Celite. The solids were washed with EtOAc. The combined filtrates were concentrated and the residue purified by chromatography to give the sub-title compound. Yield: 7.7 g (82%).

According to the analysis of related databases, 932-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; NILSSON, Peter; PELCMAN, Benjamin; KATKEVICS, Martins; WO2010/103279; (2010); A1;,
Chloride – Wikipedia,
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Application of 72934-36-2, These common heterocyclic compound, 72934-36-2, name is 1-(4-Chlorophenyl)cyclopropanamine, 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 slurry of tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (3.6 g) and 1-(4-chlorophenyl)cyclopropanamine (1.49 g) in THF (50 mL) was stirred for 5 hours at 80 C. The precipitate was filtrated through a plug washing with THF to give acrude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.8 g of tert-butyl 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate as a solid.

Statistics shows that 1-(4-Chlorophenyl)cyclopropanamine is playing an increasingly important role. we look forward to future research findings about 72934-36-2.

Reference:
Patent; Bristol-Myers Squibb Company; Wang, Tao; Scola, Paul Michael; Zhang, Zhongxing; Yin, Zhiwei; Zhao, Qian; US2013/203758; (2013); 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 102-49-8 as follows. category: chlorides-buliding-blocks

General procedure: EDC hydrochloride (1.2 mmol) and HOBt (1.0 mmol) were added at 0 °C to each parallel vial containing a solution of the appropriate acid 44-53 (1 mmol) in dichloromethane, and either cyclohexylamine or 2,3-dichlorobenzylamine (1.5 mmol) was added at the same temperature. After warming up to room temperature, the vials were placed in the Buechi Syncore reactor. Stirring was maintained at 300 rpm overnight and then morpholinomethylpolystyrene (3 equiv/mol) was added. The solutions were kept at room temperature for 1 h, then polymer bound p-toluenesulfonic acid (3 equiv/mol) was added to each vial, and the reaction mixtures were stirred at room temperature for an additional 24 h. The mixtures were filtered and the solutions were evaporated to dryness to give carboxamides 6-25. Solid products were purified by crystallization from ethanol or aqueous ethanol. Oil products were purified by silica gel column chromatography column (dichloromethane as eluent).

According to the analysis of related databases, 102-49-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Piscitelli, Francesco; Ligresti, Alessia; La Regina, Giuseppe; Gatti, Valerio; Brizzi, Antonella; Pasquini, Serena; Allar, Marco; Carai, Mauro Antonio Maria; Novellino, Ettore; Colombo, Giancarlo; Di Marzo, Vincenzo; Corelli, Federico; Silvestri, Romano; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5641 – 5653;,
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623-12-1, name is 1-Chloro-4-methoxybenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C7H7ClO

A 10 mL Schlenk reaction tube was charged with 2 mol% (8.7 mg) of a trinuclear aza-carbene palladium compound I catalyst,Methoxychlorobenzene (0.20 mmol, 28.5 mg),1-naphthylboronic acid (0.30 mmol, 51.6 mg),Potassium tert-butoxide (0.40 mmol, 44.9 mg),Then add 2mL water as solvent,80 reaction 12h.Stop the reaction,extraction,Dry and concentrate,Thin layer chromatography,Dichloromethane / petroleum ether = 1/1 gave 36.5 mg of product,Separation yield 78%.

The synthetic route of 623-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shangqiu Normal University; Wang Tao; Xu Kai; Liu Lantao; Zhao Wenxian; Liu Shuang; Li Feng; Meng Tuanjie; Xie Huanping; (12 pag.)CN105131044; (2017); B;,
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Reference of 59681-66-2, 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. 59681-66-2 name is 4-Chloro-N1-methylbenzene-1,2-diamine, 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 solution of the title compound in Example 5, Step B (0.3 mmol, 47 mg) in CH2Cl2 (0.5 mL) was added 4-trifluoromethoxyphenyl isothiocyanate (0.3 mmol, 49 muL). After 1 h MeI (0.5 mmol, 53 1L) was added. The reaction mixture was heated at 40 C for 1 h, then allowed to stand at ambient temperature for 16 h. The reaction mixture was partitioned between CH2C12 and saturated NaHCO3. The organic phase was dried with Na2S04 and concentrated in vacuo to afford a white solid. The product was isolated by flash chromatography on silica eluting with 25% EtOAc in hexanes. LC-MS (ESI, Method B): 1.67 min, m/z 342.1 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-N1-methylbenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2005/65680; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 39191-07-6, 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. 39191-07-6 name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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.

Diisopropylethylamine (0.07 mL, 0.40 mmol) was added to a mixture of 4-chloro-3-[(7-oxo-2-piperidin-1-yl-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl)-amino]-benzoic acid (0.05 g, 0.11 mmol) (from Example 61 supra) and HATU (0.076 g, 0.20 mmol) in DMF (2.0 mL). The resulting mixture was stirred at room temperature for 30 minutes. 3-Chloro-N-methylbenzylamine (Aldrich) (0.06 mL, 0.40 mmol) was added. The mixture was stirred for 18 hours and then partitioned between ethyl acetate and water. The precipitate was collected by filtration and washed with methanol and dried in vacuum oven to give 7-oxo-2-piperidin-1-yl-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid {2-chloro-5-[(3-chloro-benzyl)-methyl-carbamoyl]-phenyl}-amide. (Yield 0.040 g, 62.5%).HR-MS (ES+) m/z Calculated for C28H27Cl2N6O3 ([M+H]+): 587.1335. Found: 587.1340.

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

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 26487-67-2, 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 26487-67-2 as follows.

1-(2-Chloroethyl)azepane hydrochloride (514 mg, 2.59 mmol), 50percent NaOH (10.4 mL,12.97 mmol), and a catalytic amount of benzyltriethylammonium chloride were added to a solution of (2-phenylimidazo[2, 1 -b][1 ,3,4]thiadiazol-6-yl)methanol (120 mg, 0.52 mmol) in toluene (3 mL) under argon atmosphere. The resulting mixture was refluxed for 6 h. The reaction mixture was diluted with water and extracted withEtOAc. The organic extracts were dried with Na2504 and evaporated to dryness. The crude product was purified by silica gel column chromatography (EtOAc:MeOH mixtures of increasing polarity as eluent) to afford the desired product (393 mg, 67percent). The product was converted into the corresponding maleate salt by adding maleic acid (27 mg, 0.23 mmol) in acetone (0.25 mL), followed by filtration of the resulting solid and drying under vacuum.1H-NMR (DMSO-d6, 300 MHz) & 9.24 (s, 1H), 8.27 (s, 1H), 7.94 (m, 2H), 7.62 (m,3H), 6.00 (s, 2H), 4.55 (s, 2H), 3.78 (t, J= 5.1 Hz, 2H), 3.31 (m, 6H), 1.76 (m, 4H),1.59(m, 4H)ppm.ESI(+)-HRMS: 357.1746 [M+H].

According to the analysis of related databases, 26487-67-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; ALCALDE-PAIS, Maria de las Ermitas; DIAZ-FERNANDEZ, Jose-Luis; MESQUIDA-ESTEVEZ, Maria, de les Neus; PALOMA-ROMEU, Laura; WO2014/6130; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. category: chlorides-buliding-blocks

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 synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

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