Author: Jessica.F

Electric Literature of 93-50-5,Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, molecular formula is C7H8ClNO, 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.

A solution of 4-chloro-2-methoxyaniline (4.93 g, 31.3 mmol) in THF (70 ml) was treated with BOC-anhydride (11.00 ml, 47.4 mmol) and heated at 70 overnight. LCMS showed that most of starting materials were converted to product. The solution was treated with silica gel and evaporated under reduced pressure. The material was divided into two batches, each of which was chromatographed by Biotage MPLC (50 g silica gel column, 0 to 1% EtOAc in hexanes). Like fractions from the two columns were combined and evaporated under reduced pressure to provide a clear colorless liquid. Heptane (-80 mL) was added, then evaporated under reduced pressure to provide a clear, very viscous liquid. LCMS and NMR are consistent with tert-butyl 4-chloro-2-methoxyphenylcarbamate (7.66 g, 29.7 mmol, 95 % yield). 1H NMR (300 MHz, CHLOROFORM-d): delta ppm 8.08-7.96 (m, 1 H), 7.01 (br s, 1 H), 6.92 (dd, J=8.65, 2.20 Hz, 1 H), 6.83 (d, J=2.34 Hz, 1 H), 3.87 (s, 3 H), 1.53 (s, 9 H). LCMS: m/z 202 (loss of t-Bu).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-2-methoxyaniline, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
Chloride – Wikipedia,
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1939-99-7, name is Phenylmethanesulfonyl chloride, 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. HPLC of Formula: C7H7ClO2S

A solution of phenylmethanesulfonyl chloride (2.19 g, 10 mmol) was added into a suspension of 3-bromopropan-1-amine hydrobromide (2.19 g, 10 mmol) and Et3N (2.02 g, 20 mmol) in THF (50 mL) at 0 C. The mixture was stirred at 0 C for 5 mi TLC confirmed the completion of reaction. Solid was filtered out with suction, and the filtrate was concentrated to provide compound N-(3-bromopropyl)(phenyl)methanesulfonamide (2.7 g, quant.) as a pale yellow solid which was used in the next step without further purification. ?H NMR (300 MHz, CDC13) oe 7.40 (m, 5H), 4.48 (m, 1H), 4.27 (s, 2H), 3.41 (t, J = 6.6 Hz, 2H), 3.16 (q, 2H), 2.01 (m, 2H). LCMS (ESI), mlz, 314 and 316 [M+Na], Br pattern found.

The synthetic route of 1939-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; RENE, Olivier; WO2014/202741; (2014); 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., Recommanded Product: 4-Bromo-2-chloroaniline

Preparation 94 2-Chloro-4-(oxazol-5-yl)aniline Palladium acetate (5.4 mg, 0.024 mmol) was added to a solution of 4-bromo-2-chloroaniline (0.1 g, 0.484 mmol), oxazole (0.064 mL, 0.969 mmol), di(1-adamantyl)-n-butylphosphine (0.017 g, 0.048 mmol), pivalic acid (0.020 g, 0.194 mmol) and potassium carbonate (0.201 g, 1.453 mmol) in DMA (2.4 mL). The reaction mixture was heated at 110 C. overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35 mg, 37%). 1H NMR (500 MHz, CDCl3): delta 4.25 (br s, 2H), 6.82 (d, J=8.3 Hz, 1H), 7.20 (s, 1H), 7.38 (dd, J=8.3, 2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.87 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 2.47 min, 195 [(M+H+), 100%].

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); 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. 2106-02-7, name is 2-Chloro-4-fluoroaniline, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-4-fluoroaniline

Step 1 4-r2-Chloro-4-fluorophenylaminoV5.6.3′.4′.5′.6′-hexahvdro-2’H-?a’1bipyridinyl-2- one [l,r]-Bipiperidinyl-2,4-dione (2.00 g, 10.19 mmol) was dissolved in toluene (8 ml) and 2- chloro-4-fluorophenylamine (1.78 g, 12.23 mmol) was added. More toluene (5 ml) was added. The reaction mixture was boiled under reflux at 110 C for 17 h then allowed to cool. When the reaction mixture reached rt the product precipitated and it was collected by filtration to yield a beige solid (1.80 g, 55%). 1H-NMR (400 MHz, CDCl3) delta 7.41-7.32 (IH, m), 7.18-7.09 (IH, m), 7.00-6.90 (IH, m), 5.51 (IH, s), 5.11 (IH, s), 3.54 (2H, t), 3.38-2.67 (4H, br), 2.57 (2H, t), 1.74-1.50 (4H, m), 1.43-1.30 (2H, m).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/96151; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, 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. Recommanded Product: 1008361-80-5

To a solution of 4-bromo-3-chlorobenzene-l,2-diamine (0.15 g) and triethylamine (285 mu.) in DMF (2 mL), 90 mu. of ethyl 2-bromoacetate was added and the reaction mixture was heated at 80 C overnight. After this time, most of the volatiles were removed under reduced pressure and the residue was purified by column chromatography (silica gel, 0-2 % MeOH in DCM) to afford the title compound as a brown solid.

The synthetic route of 4-Bromo-3-chlorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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.

A stirred solution of 6-hydroxy-5-iodonicotinic acid (40 g) and DMF (3.51 mL) in toluene (315 mL) was treated dropwise with SOd2 (43.9 mL) at RT and then stirred at 85C for 2.5 h. The solvent was evaporated off under reduced pressure and the residue was redissolved in DCM (315 mL). The solution was cooled in an icy water bath and to this solution a mixture of 4-(chlorodifluoromethoxy)aniline (26 .3 g) and Et3N (63 mL) in DCM (315 mL) was added dropwise. The mixture was stirred at rt for 1 hr. Then a saturated aqueous solution of NaHCO3 was added and the mixture was stirred at rt for 10 mm and a solid was formed. The mixture was then diluted with 315 mL of hexane and filtered to collect the white solid, washed with more water and air dried to afford 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (55.97 g). (Rt = 2.28 mi +ESI m/z: MH+ = 459.0).

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

Reference:
Patent; ASTAR BIOTECH LLC; LI, Lianhai; YU, Chunrong; HUANG, Haihong; (94 pag.)WO2017/186148; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 7781-10-4, These common heterocyclic compound, 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 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 mixture of (S)-tert-butyl 2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (150 mg, 331 mumol), 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (48 mg, 286) in t-AmOH (3 mL) was added 2.0M t-BuONa in THF (286 muL, 572 mumol) then t-BuXPhos-Pd-G3 (23 mg, 29 mumol) and the resulting mixture was heated to 100 C. for 15 h, cooled to rt, and then concentrated in vacuo to give a tert-butyl (S)-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino)-2-((7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl) amino) butanoate intermediate, LCMS (ESI+): m/z=584.4 (M+H)+, which was used without further purification. Of the butanoate intermediate, 80 mg, 141 mumol) was taken up in DCM (1 mL) and TFA (400 juL) and the resulting mixture was stirred at rt for 6 h and then concentrated in vacuo. The crude residue was purified by reverse phase prep-HPLC to give the title compound. LCMS (ESI+): m/z=528.3 (M+H)+.

Statistics shows that 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine is playing an increasingly important role. we look forward to future research findings about 7781-10-4.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 1127-85-1, 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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,4-dichloro-5-fluoroquinazoline (22a) (100.00mg, 460.77 mumol, 1.00 eq) in THF (3.00mL) was added methyl (2S,3S)-3-aminobicyclo[2.2.2]octane-2-carboxylate (84.44mg, 460.77 mumol, 1.00 eq) and DIPEA (238.20mg, 1.84mmol, 4.00 eq) at room temperature overnight. H2O (20mL) was added to the mixture and extracted with EtOAc (10mL×3). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel with PE:EtOAc (10:1 to 5:1) to give compound 23a (130.00mg, 357.33 mumol, 77.55% yield) as a yellow solid.

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, 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xiong, Jian; Wang, Jingjing; Hu, Guoping; Zhao, Weili; Li, Jianqi; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 249 – 265;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14495-51-3, name is 2-Bromo-5-chlorotoluene, 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 14495-51-3, SDS of cas: 14495-51-3

13.3 ml (0.1 mol) of 2-bromo-5-chlorotoluene was dissolved in 200 ml of anhydrous THF, and 27.7 ml (0.12 mol) of triisopropyl borate was added thereto. After cooling the reaction mixture to-78C over a dry ice-acetone bath, 48 ml (0.12 mol) of 2.5 M n-BuLi (in hexane) was added dropwise thereto for 1 hour, the dry ice-acetone bath was removed, and 150 ml of 3 N HCI was added thereto. The resulting mixture was stirred for 1 hour, and the separated water layer was extracted twice with 100 ml portions of ethyl acetate. The organic layers were combined, washed with a brine solution, dried over anhydrous MgS04, and filtered under a reduced pressure to remove the solvent. The residue was recrystallized from 10% ethyacetate/hexane to obtain 13.8 g (yield 81%) of 4-chloro-2-methylboronic acid as a white solid. ¹H NMR (300 MHz, CDCh) d 8.07 (dd, 1H, J= 5.7 Hz, 2.8 Hz), 7.28-7.26 (m, 2H), 2.76 (s, 3H)

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; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; OSCOTEC INC.; WO2005/123054; (2005); 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. 344-19-4, name is 2,6-Dichloro-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H4Cl2FN

Step 1: (2,6-dichloro-4-fluorophenyl)hydrazine hydrochloride To a – 5 C solution (internal temperature, wet ice/acetone bath) of 2,6-dichloro-4-fluoroaniline (3.0 g, 17 mmol) in 37 % hydrochloric acid (30 mL) and trifluoroacetic acid (20 mL) was added dropwise an aqueous solution of sodium nitrite (1.4 g, 20 mmol, 6 mL water). The reaction was stirred for 90 minutes, then a solution of stannous chloride dihydrate (5.6 g, 25 mmol) in 37 % hydrochloric acid (16 mL) was added over 15 minutes, keeping the internal temperature ? 2 C. The mixture was stirred overnight at room temperature. The mixture was filtered and the collected solid was washed with isopropyl alcohol and dried under house vacuum to provide the title compound. LCMS-ESI+ (m/z): [M+H]+ calcd for C6H6Cl2FN2: 195.0; found: 194.9.

According to the analysis of related databases, 344-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; BLOMGREN, Peter A; CURRIE, Kevin S; GEGE, Christian; KROPF, Jeffrey E; XU, Jianjun; (60 pag.)EP3257847; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics