Tag: M.W=100-200

Synthetic Route of 10061-02-6, 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 10061-02-6 as follows.

A reactor was charged with 1.0 kg (9.0 mol) of trans-1, 3-dicloropropene, 3 L of acetonitrile and 1.02 kg (10 mol) of sodium bromide. The suspension was heated to reflux for at least 24 hours, then cooled to 20/250C at the end of the reaction; the salts were filtered and washed with 2 x 500 mL of acetonitrile. The filtrate was distilled through a Vigreux column at atmospheric pressure and internal temperature of 80/l00C to remove the acetonitrile, getting 1.096 kg of a dark orange oil. Weight composition by 1H-NMR: 89% of trans-3-bromo-l- chloropropene, 8% of trans-1, 3 -dicloropropene and 3% of solvent. 1H NMR (CDC13) delta: 3.93 (m, 2H, CH2), 6.14 (m, IH, CH), 6.33 (dt, IH, CHCl). MS (EI) m/z: 156 (M+), 77.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.I.S. FABBRICA ITALIANA SINTETICI S.p.A; WO2008/6394; (2008); A1;,
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Electric Literature of 501-29-1, 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 501-29-1 as follows.

A mixture of 4-chloro-3-fluoroanisole (2.52 g, 15.7 mmol, 1.0 eq.), silver trifluoroacetate (8.57 g, 38.8 mmol, 2.5 eq.), iodine (7.95 g, 31.3 mmol, 2.0 eq.) and chloroform (100 mL) is stirred at r.t. for 16h. The reaction mixture is filtered through a silica plug on a fritted funnel and rinsed with chloroform. The filtrate is washed successively with an aqueous solution of Na2S2O3, water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel to afford the expected product

According to the analysis of related databases, 501-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; DE CEUNINCK, Frederic, Andre; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (180 pag.)WO2017/211666; (2017); A1;,
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Reference of 4584-46-7, 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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-(2,4-dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dione (317 mg, 1.01 mmol), 2-dimethylaminoethyl chloride hydrochloride (160 mg, 1.11 mmol) and potassium carbonate (350 mg, 2.5 mmol) in DMF (4 mL) was heated at 60 C. for 18 hours. The mixture was concentrated in vacuo, taken up in ethyl acetate and extracted twice with 1N hydrochloric acid. The aqueous extracts were made basic with solid potassium carbonate and extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give the title compound (236 mg, 61%) as an off-white solid. 1H NMR (methanol-d4) 7.73 (1H, t), 7.44-7.40 (2H, m), 7.02 (1H, d), 6.51 (1H, d), 6.42 (1H, dd), 4.72 (2H, s), 4.33 (2H, t), 3.80 (3H, s), 3.76 (3H, s), 2.87 (2H, t), 2.40 (6H, s). MS: [M+H]+ 385.

The synthetic route of 2-Chloro-N,N-dimethylethanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
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Synthetic Route of 445-14-7, 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 445-14-7 as follows.

40% HBr (2.20 mL, 15.34 mmol) was dissolved in H2O (2 mL), then at 0 C,2-Amino-4-chlorobenzotrifluoride (0.50 g, 2.56 mmol) was added to the reaction mixture, followed by 0 C,An aqueous solution of sodium nitrite (sodium nitrite (0.21 g, 3.07 mmol) dissolved in 2 mL of water) was added dropwise to the reaction mixture.After the reaction solution was stirred at 0 C for half an hour, additional cuprous bromide (0.63 g, 4.35 mmol) of 40% HBr (2.20 mL, 15.34 mmol) andA mixed solution of H2O (3 mL).The reaction solution was stirred at 75 C for 3 hours, and then cooled to room temperature.It was then extracted with ethyl acetate (40 mL x 4).The combined organic phases were washed with brine (80 mL x 2).Dry with anhydrous Na2SO4,The title compound was obtained as a yellow liquid after concentration under reduced pressure.(0.76g, 100%).

According to the analysis of related databases, 445-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Xiaobo; Zhou Shiqing; (62 pag.)CN103833753; (2017); B;,
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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. Quality Control of 3-Chloro-2-fluoroaniline

A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), l-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel() bromide at RT under N2. The concentration was halved by die introduction of additional NMP under N2 and the solution was gently warmed to 200+/- 5C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of teft-hutyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (~30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2106-04-9, its application will become more common.

Reference:
Patent; CYTOKINETICS, INC.; WO2007/70683; (2007); A2;,
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Synthetic Route 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.

3-chloro-2-fluoroaniline (0.239 mL, 2.17 mmol) was added to a stirred suspension of methyl 8-(l-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (215 mg, 0.54 mmol) dissolved in DCM (3 mL) at room temperature. The resulting suspension was stirred for 16 hrs then the temperature was increased to 50C for 16 hrs. The crude product was purified by flash chromatography on silica gel eluting with 5% methanol in DCM. The solvent was evaporated to dryness to afford methyl 8-(l-(3-chloro-2- fluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (206 mg, 82 %) as a white solid. Mass Spectrum: M+H+ 461.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2-fluoroaniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard, Christophe; DEGORCE, Sebastien, Louis; LAMBERT-VAN DER BREMPT, Christine, Marie, Paul; MORGENTIN, Remy, Robert; PLE, Patrick; WO2011/51704; (2011); A1;,
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29027-20-1, name is 3-Chloro-5-methylaniline, 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. SDS of cas: 29027-20-1

to the mixture of solid (400 mg, 1.66 mmol) from Step 2-1 and MeOH (15 mL) was added 3-chloro-5-methylaniline (0.21 mL, 1.66 mmol), formic acid (0.064 mL, 1.66 mmol) and l-(2,2-dimethoxy-ethyl)-2- isocyano-benzene ( 0.32 mL, 2.5 mmol). The resulting mixture was heated at 50 C overnight. The reaction solution was concentrated and dried under high vacuum to give brown solid as the desired product (60% pure). The crude material was used for next step without further purification.

The synthetic route of 29027-20-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRINETICS PHARMACEUTICALS, INC.; ZHAO, Jian; ZHU, Yunfei; WANG, Shimiao; HAN, Sangdon; KIM, Sun Hee; (109 pag.)WO2017/3724; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Formula: C7H7ClFN

To a solution of (4-chloro-3-fluorophenyl)methanamine (266 mg, 1.67 mmol, Alfa) in a methanol buffer (3.6 weight % sodium acetate trihydrate and 2.4 weight % acetic acid in methanol, l5mL) was added 1,4-dioxane-2,5-diol (100 mg, 0.833 mmol, Aldrich) in one portion followed by sodium cyanoborohydride (105 mg, 1.67 mmol) and trifluoroacetic acid (0.1 mL). After stirring at ambient temperature for 10 minutes, the reaction mixture was concentratedunder reduced pressure to less than 5 mL and was filtered through a glass microfiber frit, and then purified by preparative HPLC [YMC TriArtTM Cl 8 Hybrid 5 jim column, 50 x 100 mm, flow rate 140 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (0.18 g, 0.88 mmol, 53.0 % yield). MS (ESf?) nilz 204 (M+H).

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Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen Ann; SIDRAUSKI, Carmela; FROST, Jennifer M.; SHI, Lei; TONG, Yunsong; DART, Michael J.; MURAUSKI, Kathleen; (213 pag.)WO2019/90088; (2019); A1;,
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Chlorides – an overview | ScienceDirect Topics

Application of 1435-48-9, A common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, 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 2,4-Dichloro-1-fluorobenzene (8.0 g, 48.5 mmol) in THF (63 mL) n-BuLi (23.27 mL, 2.5 M, 43.6 mmol) was added dropwise at -78 C and stirred for 1.5 h. To the mixture Sulfur (3.1 g, 72.7 mmol) was added at -78 C and stirring for 2 h. To the resulting mixture 10% Hydrochloric acid (HCl) was added to adjust pH to 5-6. The resulting mixture was extracted with EtOAc (200 mL * 3), the combined organic phase was washed with brine (100 mL * 2), dried over Na2SO4. After filtered, the organic phase was concentrated to dry to give compound 31 as yellow oil (11.4 g, 99.0% yield). 1H NMR (400 MHz, CDCl3) delta 7.31-7.19 (m, 1H, Ar-H), 6.95-6.89 (t, 1H, Ar-H), 4.69 (s, 1H, SH).

The synthetic route of 1435-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Na; Wang, Yanfen; Huang, Gongchao; Ji, Conghui; Fan, Wei; Li, Haitao; Cheng, Ying; Tian, Hongqi; Bioorganic Chemistry; vol. 65; (2016); p. 146 – 158;,
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These common heterocyclic compound, 75717-77-0, name is 2,4-Dichlorophenylacetylene, 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. COA of Formula: C8H4Cl2

Was added quinoline (65 ~ 84.5mg, 0.5 ~ 0.65mmol) in a round bottom flask, 2,3-dichlorobenzene acetylene (85mg, 0.5mmol), trifluoromethyl propiolate (114mg, 0.75mmol), cuprous iodide (9.5mg, 10% mol), dichloromethane(5mL) as a solvent, at room temperature for 24 to 30 hours; then spin dry instead of dimethyl sulfoxide as solvent, was added copper bromide (11.2mg, 10% mol), 4- dimethylaminopyridine (12.2mg, 20% mol) 100 ~ 120 after heating the reaction to 18 to 24 hours,After cooling to room temperature with saturated brine and extracted three times with ethyl acetate, the organic layers were spin-dry column chromatography to give the pure productionThereof. As a pale yellow solid. Yield 52%.

The synthetic route of 2,4-Dichlorophenylacetylene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai University; Xu, Zhiliang; Chen, Jie; Han, Jing; Zhang, Hui; Cao, Weiguo; (19 pag.)CN105669667; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics