Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 18655-50-0, name is 3-(4-Chlorophenyl)propan-1-amine, 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 18655-50-0, HPLC of Formula: C9H12ClN

Example 170 N-[3-(4-Chlorophenyl)propyl]-4-oxo-4-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butanamide Using 4-oxo-4-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butanoic acid obtained in Reference Example 16 and 3-(4-chlorophenyl)propylamine obtained in Reference Example 23, the title compound was obtained as oily matter by the same procedure as in Example 12. 1H-NMR (CDCl3) delta: 1.73-1.85 (2H, m), 2.60 (4H, m), 3.05 (4H, m), 3.24-3.34 (4H, m), 3.77-3.80 (4H, m), 5.87 (1H, m), 7.09-7.28 (5H, m), 7.77 (2H, m).

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

Reference:
Patent; Ishihara, Yuji; Terauchi, Jun; Suzuki, Nobuhiro; Takekawa, Shiro; Aso, Kazuyoshi; US2003/158177; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products 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.

6-ACETOXY-4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXYQUINAZOLINE HYDROCHLORIDE 6-ACETOXY-4-CHLORO-7-METHOXYQUINAZOLINE (prepared as described in Example 25-5 of in WO01/66099, 6.00 g, 23.8 mmol) and 3-chloro-2-fluoroaniline (3.46 g, 23.8 mmol) were suspended in iso-propanol (200 ML). The mixture was heated to 80C under reflux for 3 hours. The solvent was evaporated; the residue was crystallised from acetonitrile, giving the product hydrochloride as a pale pink crystalline solid (8.16 g, 92%); H NMR : 2.37 (s, 3H), 4.00 (s, 3H), 7.34 (ddd, 1H), 7.48 (s, 1H), 7.52 (ddd, 1H), 7.61 (ddd, 1H), 8.62 (s, 1H), 8.86 (s, 1H) ; Mass Spectrum : 362. 4,364. 4.

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; WO2005/28469; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, 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 1303587-99-6, Application In Synthesis of 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine

Synthesis of2-chloro-8-(2, 2, 2-trifluoroethyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0414] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (500 mg, 2.92 mmol) in DMF (5 mL) under argon atmosphere were added cesium carbonate (1.9 g, 5.84 mmol) and 1, 1, l-trifluoro-2-iodoethane (611 mg, 2.92 mmol) at RT and the mixture was stirred for 32 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 silica gel column chromatography using 20% EtOAc:hexanes to afford 2-chloro-8-(2, 2, 2-trifluoroethyl)-7, 8-dihydro-6H-pyrimido [5, 4- b] [1, 4] oxazine (235 mg, 32%) as an off-white solid. 1H-NMR (CDC13, 500 MHz): delta 7.79 (s, 1H), 4.30-4.28 (m, 2H), 4.27-4.23 (m, 2H), 3.70-3.68 (m, 2H); LC-MS: 254.4 (M+1); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.76 min. 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc:hexanes (R/. 0.6).

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; 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, 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 106131-61-7 as follows.

General procedure: To a solution of DIPEA (2.1 mmol) in acetonitrile (150 mL) which was preheated to 70 C was added dropwise a solution of 3,6-dihydroxyphthalimide derivatives 1a-e (1 mmol) and 3,6-dichlorotetrazine (2, 1 mmol) in acetonitrile (25 mL) during 25 min. After being stirred for another 5 min, the reaction was quenched by cooling down the mixture to ambient temperature and adding water (200 mL). The resulting mixture was neutralized with dilute hydrochloric acid (1 M) and extracted with EtOAc (3 × 150 mL). The combined organic solution was washed with brine (3 × 200 mL) and then dried over anhydrous Na2SO4. After filtration and concentration, the residue was chromatographed on a silica gel column using a mixture of DCM and EtOAc (v/v = 100:1) as an eluent to give product 3a-e.

According to the analysis of related databases, 106131-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gu, Meng-Di; Lu, Yao; Wang, Mei-Xiang; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1976 – 1983;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-02-7, 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. 2106-02-7, name is 2-Chloro-4-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of2-chloro-N-(2-chloro-4-fluorophenyl)-5-methoxypyrimidin-4-amine [0431] To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (5 g, 27.93 mmol) in DMF (50 mL) under argon atmosphere were added sodium hydride (1.3 g, 55.86 mmol) and 2-chloro-4-fluoroaniline (4 g, 27.93 mmol) at 0 C. The reaction mixture was warmed to RT and stirred for 16 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with ice water (50 mL) to afford the solid which was filtered, washed with water and dried in vacuo to afford 2-chloro-N-(2-chloro-4-fluorophenyl)-5- methoxypyrimidin-4-amine (3.5 g, 44%) as an off-white solid. 1H-NMR (DMSO-< 5, 400 MHz): delta 9.10 (s, 1H), 7.92 (s, 1H), 7.61-7.55 (m, 2H), 7.29 (t, 1H), 3.93 (s, 3H); LCMS: 288.2 (M+); (column; X-Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.76 min. 5 mM Aq NH4OAc: ACN; 0.80 mL/min); TLC: 10% EtOAc:hexanes (R 0.5). In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-4-fluoroaniline, other downstream synthetic routes, hurry up and to see. 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

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. 7006-52-2, name is N-Methyl-3-chloroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 7006-52-2

[0299] To a mixture of the compound Int-11 (Example 130) (200 mg, 0.58 mmol, 1.0 eq) in DCM (10 rriL) was added 3-chloro-N-methylaniline (82.4 mg, 0.58 mmol, 1.0 eq), triethylamine (176 mg, 1.74 mmol, 3.0 eq) and DMAP (14.6 mg, 0.12 mmol, 0.2 eq). The mixture was stirred at r.t. overnight under nitrogen atmosphere. The reaction was monitored by LCMS. DCM (10 mL) was added and the resulting mixture was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 53 mg of the desired Compound 131 (20percent yield) as a light yellow solid in >95percent purity as determined by HPLC analysis. 100percent HPLC purity at 254 nm. 1H-NMR (400 MHz, DMSO-d6): delta 10.86 (s, 1H), 9.01 (dd, J = 4.0, 1.6 Hz, 1H), 8.70 (s, 1H), 8.45 (d, J = 7.6 Hz, 1H), 8.22-8.19 (m, 2H), 8.14-8.07 (m, 2H), 7.64 (dd, J = 8.0, 4.0 Hz, 1H), 7.57 (t, J = 8.0 Hz, 1H), 7.42-7.33 (m, 2H), 7.23-7.10 (m, 3H), 3.17 (s, 3H); ESI/MS [m/z] = 452 [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; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); 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 1939-99-7 as follows. name: Phenylmethanesulfonyl chloride

To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0 C. was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N.HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel column chromatography (0-30% Acetone in heptane, 216 nM) to N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenylmethanesulfonamide (17.8 g, 81% yield). LCMS (ESI), m/z, 330. [M+H]+.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Fauber, Benjamin; Gobbi, Alberto; Rene, Olivier; Bodil van Niel, Monique; Gancia, Emanuela; Gaines, Simon; Laddywahetty, Tammy; Vesey, David; Ward, Stuart; Winship, Paul; US2015/197529; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrClN

To a solution of 4-bromo-2-chloroaniline 60 (2.50 g, 12.11 mmol) in acetic acid (25 ml) was added at room temperature potassium thiocyanate (4.71 g, 48.4 mmol). To the mixture was dropped for 15 minutes a solutions of bromine (1.25 ml, 24.22 mmol) in acetic acid (5 ml). After the end of dropping, it was stirred at room temperature for 15 minutes and further stirred at 30 C for 1 hour. After the end of the reaction, the mixture was neutralized with aqueous sodium hydroxide under ice-cooling and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and brine, respectively and dried over sodium sulfate. The solvent was evaporated under reduced pressure. To the residue was added ethyl acetate and di-isopropyl ether. The mixture was filtered to give Compound 61 (2.02 g, yield 43.3%) as a yellow solid. 1H-NMR (DMSO-d6) delta: 7.48 (dd, J= 2.1, 0.9 Hz, 1H), 7.89 (dd, J= 2.7, 1.8 Hz, 1H), 7.97 (brs, 2H).

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; Shionogi & Co., Ltd.; EP2351744; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 202925-07-3, name is 2-Chloro-1-fluoro-4-methoxybenzene, 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. Application In Synthesis of 2-Chloro-1-fluoro-4-methoxybenzene

To 2-chloro-1-fluoro-4-methoxybenzene (5 g) in methylene chloride (30 ml) solution, titanium tetrachloride (5.8 ml) and alpha,alpha-dichloromethylmethylether (2.8 ml) were added under ice cooling, the mixture was stirred at 2C for 11.5 hours, then the reaction solution was poured into ice. Next, the methylene chloride layer was separated, washed with saturated saline, dried over with anhydrous sodium sulfate, and concentrated. The obtained residue was recrystallized from ethylether. The thus obtained 4-chloro-5-fluoro-2-methoxybenzaldehyde (3.41 g) was used instead of the starting material in Reference Example 2, that is, the compound S1, for successively the similar procedure as in Reference Example 2 to Reference Example 6 to obtain the title compound. NMR (CDCl3): delta7.96(1H, s), 7.37(1H, d, J=9.0Hz), 7.06(1H, br), 6.96(1H, d, J=5.9Hz), 4.33(2H, d, J=6.1Hz), 3.84(3H, s) MS: 378(M+Na)+

The synthetic route of 2-Chloro-1-fluoro-4-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asubio Pharma Co., Ltd.; Daiichi Sankyo Company, Limited; EP2025672; (2009); 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. 849367-49-3, name is 3-Bromo-4-chlorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H7BrClN

N-[(3-Bromo-4-chlorophenyl)methyl]-N’-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}butanediamide In a 100 mL round-bottomed flask was added 4-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-4-oxobutanoic acid (1.0 g, 2.478 mmol), 1-(3-bromo-4-chlorophenyl)methanamine (0.595 g, 2.7 mmol), HATU (1.065 g, 2.8 mmol) and triethylamine (0.641 ml, 4.6 mmol) in dichloromethane (35 mL) to give a yellow suspension. The mixture was stirred overnight at room temperature. The reaction was quenched with saturated NaHCO3 and diluted with DCM. The organic layer were separated, then washed with water followed by saturated NaCl. The organic layer was dried over Na2SO4 and evaporated to a small volume, about 15 mL, from which a crystalline solid appeared which was collected, washed very sparingly with DCM and dried to give N-[(3-bromo-4-chlorophenyl)methyl]-N’-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}butanediamide (1 g, 66.6%) as a solid. LC-MS m/z 605.5 (M+H)+, 0.75 min (ret time).

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 849367-49-3.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics