Month: May 2021

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

Application of 26487-67-2, A common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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.

Add sodium hydride (18 g, 0.45 mol) into a solution of 4-benzyloxylphenol (41 g, 0.20 mol) and 2- (hexamethyleneimino) ethyl chloride hydrochloride (44 g, 0.22 mmol) in THF (600 mL) and DMF (100 mL) at room temperature. Heat to 60°C for 30 minutes. Pour the solution into ice and water. Dilute with ethyl acetate (500 mL) and separate layers. Dry the organic layer with magnesium sulfate, filter and concentrate under reduced pressure to give brown oil. Dissolve the oil in ethyl acetate (500 mL) and methanol (500 mL). Add ammonium formate (100 g, 1.59 mol) and palladium on carbon (10 g, 9.4 mmol). Heat the mixture to reflux for 30 minutes. Add ammonium formate (100 g, 1.59 mol) and palladium on carbon (10 g, 9.4 mmol). Heat the reaction mixture for 30 minutes. Filter the supension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2 x 200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 31 g (64 percent) of4- (2-azepan-l-yl- ethoxy)-phenol. Combine 2-benzyloxy-1-bromo-6-methoxy-naphthalene (31 g, 90 mmol), 4- (2- azepan-l-yl-ethoxy)-phenol (31 g, 132 mmol), copper bronze (12 g, 189 mmol), potassium carbonate (25 g, 181 mmol) and pyridine (400 mL). Heat the reaction mixture to reflux for 85 hours. Cool and filter the residue with celite and elute with methanol and methylene chloride (500 mL, Vu = 1 : 5). Evaporate solvent under reduced pressure and chromatograph the residue on a silica gel column eluting the material with a step gradient of methanol/dichloromethane (0 to 10percent) to get 19 g (43percent) of 1- {2- [4- (2-benzyloxy-6- meCoxy-naphthalen-l-yloxy)-phenoxyl-ethyl}-azepane. Dissolve 1- {2- [4- (2-benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}- azepane (19 g, 38 mmol) in ethyl acetate (500 mL) and methanol (600 mL). Heat the mixture to obtain a clear solution. Cool to room temperature. Add ammonium formate (30 g, 476 mmol) and palladium on carbon (2 g, 1. 9 mmol). Heat to reflux for 30 minutes. Add ammonium formate (7 g, 111 mmol) and palladium on carbon (0.7 g, 0.7 mmol). Heat to reflux for 30 minutes. Filter the supension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2 x 200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 15.1 g (97percent) of 1- [4- (2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-napbthalen-2-ol. Add trifluoromethanesulfonic anhydride (7 mL, 42 mmol) into a solution of 1- [4- (2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-naphthalen-2-ol (15 g, 37 mmol), triethylamine (20 mL) and methylene chloride (500 mL) at-50°C. Warm the reaction mixture to room temperature and stir for 1 hour at that temperature. Cool the reaction mixture to-78°C and add brine (20 mL). Warm the reaction to room temperature. Separate layer and wash the organic layer with saturated sodium bicarbonate solution (100 mL) and brine. Dry the organic layer with magnesium sulfate, filter and evaporate solvent under reduced pressure. Chromatograph the residue on a silica gel column eluting the material with a step gradient of methanol/dichloromethane (0 to 10percent) to get 20 g (99percent) of trifluoro-methanesulfonic acid 1- [4-(2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy- naphthalen-2-yl ester.

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4152-90-3, These common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, 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.

N-(3-Chlorobenzyl)-5-fluoro-2-nitrobenzenamine:; 2,4-Difluoronitrobenzene (2.9 g, 18.1 mmol), 3-chlorobenzylarnine (2.6 g, 18.1 mmol) 0 and LambdazetaiV-diisopropylethylamine (2.4 g, 18.1 mmol) were stirred in acetonitrile (25 mL) at room temperature for 2 hours. The solvent was evaporated and the crude mixture was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated in vacuo to collect the title compound (4.8 g, 95 percent yield). 1H NMR (400 MHz, CDCl3): delta 8.55 (s, IH), 8.25 (dd, IH), 7.32-7.21 (m, 4H), 6.41 (m, 2H), 4.50 (d, 2H).

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

Reference:
Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2006/81332; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 24279-39-8, 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. 24279-39-8, name is 2,6-Dichloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6; Ethyl 2- {5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4- YL} CYCLOPROPANECARBOXYLATE; To a stirred solution OF 2, 6-DICHLORO-4- (TRIFLUOROMETHYL) PHENYLAMINE (3.0 g, 13 mmol) in ethanol (3 MT) at–5C was added TETRAFLUOROBORIC acid (48% in water, 27.3 MINOT). To the mixture was added isoamyl nitrite (1.8 ml, 13. 6 MMOL), dropwise over 10 min, and the reaction mixture was stirred for 30 min at room temperature. The solid was filtered and WASHED-WITB ETHANOL, followed by diethyl ether,. to give. the diazonium salt (3.2g, 9. 73 NIMOL, 75%) as a white solid. To a solution of Preparation 6 (50 mg, 0.20 mmol) in acetonitrile (2 ml) at 0C was added diazonium-salt (65 mg, 0.20 mmol). The reaction mixture was then allowed to warm to room temperature with stirring. The solution was concentrated under a stream of nitrogen and to the residue was added dichloromethane (2. 5 ml), ammonia (0.880, 2.5 ml) and water (2.5 ml), with vigorous stirring. The. mixture was partitioned between water (20 ml) and dichloromethane- (20 ml) and the two layers were separated. The aqueous layer was extracted with dichloromethane (2 X 10 ml) and the combined organic layers were dried (NA2SO4) and concentrated in vacuo. The residue was loaded on to an ABSOLUTE column (silica, 2 g) in a mixture of cyclohexane and dichloromethane mixture (4 :-1) and eluted with cyclohexane : ethyl acetate [1 : 0 to 3 : 7]. The appropriate fractions were combined and concentrated to give the product (15 mg, 0, 03 mmol, 17 %) as an orange oil. MS (ES) M/Z [MH+]. = 433. 42,. C17H13C12F3N402 +H REQUIRES 433. 04459. NMR (CDC13, selected data): 1.35 (t, 3H), 1.6-1. 7 (m, 2H), 1. 9- 2.0 (m, 1H), 2.0-2. 1 (m, 1H), 3.65 (S, 2H), 4. 2 (q, 2H), 8.8 (M, 2H).

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, 2,6-Dichloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/23773; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9, COA of Formula: C3H4Cl3NO

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.683 (s, 1H), 8.03 (s, 1H), 7.91 (d, 1H), 7.89 (d, 1H), 4.31 (s, 3H); 13C NMR (400 MHz, CDCl3) 146.93, 146.46, 124.52, 121.24, 115.70, 115.27, 41.06; MS (+ve ES) 178 (M+H).

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:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57946-56-2, name is 4-Chloro-2-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 57946-56-2, Safety of 4-Chloro-2-fluoroaniline

Hydrogen chloride (6.5 M, 2.54 mL) was added to a mixture of compound 1 (4.51 g, 15.0 mmol) and 4-chloro-2-fluoroaniline (2.40 g, 16.5 mmol) in 2-propanol (160 mL), then the mixture was heated at reflux for 2 h. The mixture was cooled and solid was filtered. The solid was then washed with 2-propanol, followed by Et2O, and dried under vacuum overnight to give 2a (7.9 g, 94%) as a white solid.

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:
Article; Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3222 – 3226;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics