Month: August 2021

Electric Literature of 13078-79-0, 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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 15 [2-(3-Chloro-phenyl)-ethyll-f4-(6-fluoro-lH-indol-4-yl)-6-morpholin-4-yI- p yrimidin-2-yIl -amine; A mixture of 6-fluoro-4-(2-methanesulfonyl-6-mophiholin-4-yl-pyrimidin-4-yl)- 1 H- indole (75 mg, 0.20 mmol) and 3-chlorophenethylamine (310 mg, 2.00 mmol) in DIPEA (0.1 mL, 0.57 mmol) and dioxane (0.4 mL) were heated in a microwave reactor at 150C for 40 minutes. The reaction mixture was purified by preparative HPLC to yield the title compound as an off-white solid (71 mg). deltaH (400MHz, CDCl3) 2.86 (t, J = 7.1, 2H), 3.58 (t, J = 4.5, 4H), 3.66 (q, J = 6.6, 2H), 3.73 ( t, J = 4.7, 4H), 4.90 (br s, IH), 6.29 (s,lH), 6.91 (s, IH), 7.06 (d, J = 8.2, 2H), 7.10-7.20 (m, 4H), 7.25 (d, J = 10.0, IH), 8.15 (br s, IH). [M + H]+ 452.10

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-(3-Chlorophenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125839; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 7051-16-3, 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 7051-16-3 as follows.

To a mixture of 5-chloro-1,3-dimethoxybenzene (1.73 g, 10.0 mmol) dissolved in dichloromethane (60 mL) was slowly added boron tribromide (ca. 1.0 M, dichloromethane solution, 40 mL, 40 mmol, 4.0 equiv) at -78 C. After gradually warming to room temperature, the mixture was stirred for 3 days, and to this was added an aqueous saturated solution of sodium bicarbonate (50 mL). The mixture was extracted with dichloromethane (50 mL × 3), and the combined organic extract was washed with brine (20 mL), dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica-gel 50 g, n-hexane/CH2Cl2= 1/1) to give 5-chlororesorcinol (1.39 g, 9.59 mmol, 95.9%) as a colorless solid.

According to the analysis of related databases, 7051-16-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Uchida, Keisuke; Yoshida, Suguru; Hosoya, Takamitsu; Synthesis; vol. 48; 23; (2016); p. 4099 – 4109;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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 1-(2-Chloroethyl)azepane hydrochloride

EXAMPLE 9 To a solution of 7.5 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in a solvent mixture comprising 30 ml of a 10percent aqueous sodium hydroxide solution and 30 ml of methanol is added dropwise under ice cooling with stirring an aqueous solution of 7.0 g of 1-chloro-2-(perhydroazepin-1-yl)ethane hydrochloride over a period of about 10 minutes, and the resulting mixture is stirred at room temperature for 4 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is rinsed with a 5percent aqueous sodium hydroxide solution, washed with water and dried. Thereafter the solvent is distilled off to obtain an oily residue of 2-(2-perhydroazepin-1-ylethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine. The oily product thus obtained is treated, according to usual procedure, with 2.74 g of fumaric acid and recrystallized from isopropyl alcohol to obtain 9.9 g of 2-(2-perhydroazepin-1-ylethylthio)-5-(2-chlorophenyl)-7 -chloro-3H-1,4-benzodiazepine fumarate, m.p. 170°-171° C. Elementary analysis: for C23 H25 N3 SCl2.C4 H4 O4: Calculated: C: 57.65, H: 5.20, N: 7.47; Found: C: 57.76, H: 5.31, N: 7.40.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26487-67-2, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4094870; (1978); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 53531-69-4, 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 53531-69-4 as follows.

Step a) Intermediate 204 l-(4-Bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4-yl)methanesulfonamide To a suspension of N-methyltetrahydro-2H-pyran-4-amine (0.507 g, 4.40 mmol) and sodium carbonate (0.467 g, 4.40 mmol) in MeCN (10 ml) was added (4- bromophenyl)methanesulfonyl chloride (0.593 g, 2.201 mmol) and the reaction mixture was stirred at r.t. for 1.5 h. The mixture was quenched with water and extracted with EtOAc (x 2). The organics were dried (MgS04) and concentrated under reduced pressure to yield l-(4-bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4- yl)methanesulfonamide as a white solid (0.634 g, 83 %). ? NMR (400 MHz, MeOD) delta 7.56 (m, 2H, J = 8.34 Hz), 7.38 (m, 2H, J = 8.34 Hz), 4.34 (s, 2H), 3.95 (dd, 2H, J = 1 1.62, 4.55 Hz), 3.69 – 3.82 (m, 1H), 3.35 – 3.43 (m, 2H), 2.72 (s, 3H), 1.74 – 1.87 (m, 2H), 1.45 – 1.53 (m, 2H)

According to the analysis of related databases, 53531-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); 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. 87851-77-2, name is O-(3-Chloroallyl)hydroxylamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of O-(3-Chloroallyl)hydroxylamine

2. Preparation of (E)-2-[1-(3-chloro-2-propenyloxyimino)propyl]5-(1-methyl-1H-pyrazol-4-yl)cyclohexane-1,3-dione (Compound No. 1) STR15 To 200 ml of an ethanolic solution of 20.0 g (81 mmols) of 5-(1-methyl-1H-pyrazol-4-yl)-2-propionylcyclohexane-1,3-dione was added 210 ml (84 mmols) of 0.4 mol ethanolic solution of (E)-3-chloro-2-propenyloxyamine. The mixture was reacted for 8 hours with stirring. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate) to give 12.5 g of the product. Physical properties: Melting point, 99° C. Yield, 46percent. 1 H NMR (CDCl3, TMS), ppm. delta1.13 (3H, t, J=7 Hz) 2.4-3.7 (7H, m) 3.83 (3H, s) 4.49 (2H, d, J=6 Hz) 5.9-6.5 (2H, m) 7.16 (1H, s) 7.29 (1H, s).

According to the analysis of related databases, 87851-77-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; US4863504; (1989); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1008361-80-5, A common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

[0660] A mixture of 4-bromo-3-chlorobenzene-1,2-diamine (0.2 g) and oxalic acid (90 mg) in 4N aq. HC1 was refluxed for 5 h. The heterogeneous mixture was then cooled to room temperature and the solid was isolated by filtration. This brick-red solid was washed thoroughly with water and dried under high vacuum. Used as such for the next step (Following the procedure from Organometaiics 2014, 33, 16 17-1622).

The synthetic route of 1008361-80-5 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; (394 pag.)WO2017/35360; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 51572-93-1, 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. 51572-93-1 name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, 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.

General procedure: To a solution of 3ae3e (1 mmol) in anhydrous ethanol (10 mL),corresponding O-benzylhydroxylamine hydrochloride (1 mmol)and NaOAc (1.2 mmol) were added and the resulting solution wasstirred at the room temperate for 3 h. The mixture was concentratedand taken in ethyl acetate (20 mL), washed with water(20 mL), saturated sodium chloride solution (20 mL) and dried oversodium sulfate. The resulting solution was concentrated and thepurification of the residue by recrystallization from ethanol yieldedthe desired compounds 4a-4t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Lv, Xian-Hai; Li, Qing-Shan; Ren, Zi-Li; Chu, Ming-Jie; Sun, Jian; Zhang, Xin; Xing, Man; Zhu, Hai-Liang; Cao, Hai-Qun; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 586 – 593;,
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. 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Quality Control of 4-(Chlorodifluoromethoxy)aniline

To a solution of (R)-9-bromo-4-hydroxy1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-carboxylic acid (38d, 30 mg, 0.096 mmol) in DMF (2 mL) was added HATU (54.99 mg, 0.145 mmol), DIEA (124.62 mg, 0.964 mmol, 167.95 uL) and 4-[chloro(difluoro)methoxy]aniline (1h, 28.00 mg, 0.145 mmol). The mixture was stirred at 15 C. for 16 hr. TLC (ethyl acetate_methanol=10:1, Rf=0.3) indicated a new spot was generated. LCMS showed a peak with desired MS was detected. The mixture was quenched with water (20 mL) and the mixture was extracted with ethyl acetate (30 mL*3). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by prep-TLC (ethyl acetate_methanol=10:1, Rf=0.3) to give 38e as a yellow solid.

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; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 16793-91-2,Some common heterocyclic compound, 16793-91-2, name is 2-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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.

Example 14: Preparation of 8-[2-(2-chlorophenyl)ethyl]-3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8-azaspiro[4.5]dec-3-en-2-one [Show Image] A mixture of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8-azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 200 mg, 0.40 mmol), anhydrous potassium carbonate (180 mg, 1.30 mmol) and 1-(2-bromo-ethyl)-2-chlorobenzene (0.07 mL, 0.22 mmol) in anhydrous N,N-dimethylformamide (3 mL) was heated at 90C for 1.5 hours under microwave irradiation. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane (20 mL), washed with water (20 mL) and brine (20 mL), dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid (76 mg, 34%). 1H NMR (DMSO-d6, 400 MHz): delta 7.46-7.34 (m, 3H), 7.26-7.23 (m, 4H), 7.11 (d, J = 7.5 Hz, 1 H), 3.80-3.79 (m, 1H), 3.68-3.69 (m, 1H), 3.56 (s, 2H), 3.27 (s, 1H), 3.16-3.15 (m, 2H), 2.93-2.92 (m, 1H), 2.87-2.83 (m, 4H), 2.53 (s, 2H), 2.25-2.24 (m, 3H), 1.88-1.87 (m, 1H), 1.76 (s, 3H), 1.72 (s, 1H), 1.52 (s, 1H). LCMS (Method D): Mass found (M+ 562), Rt (min): 4.64, Area (%): 99.5 (Max), 99.6 (254 nm). HPLC (Method A): Rt (min): 4.61, Area (%): 98.5 (Max), 99.3 (254 nm).

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

Reference:
Patent; Ares Trading SA; EP2508526; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 38762-41-3, A common heterocyclic compound, 38762-41-3, name is 4-Bromo-2-chloroaniline, molecular formula is C6H5BrClN, 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 2,3,4-trifluorobenzoic acid (1 g, 5.68 mmol) and 4-bromo-2- chloroaniline (1.2 g, 5.68 mmol) in acetonitrile (10 mL) was added lithium amide (0.39 g, EPO 17.04 mmol) and the reaction stirred at 60 0C for 1.5 hours. The mixture was cooled to room temperature and then to 0 0C and acidified with aq. hydrochloric acid. The obtained precipitate was collected by filtration and washed with cold water and dried in vacuo to afford 2-[(4~bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acid (1.92 g, 94% yield) as a beige solid. MS (EI) for C13H7BrClF2NO2: 363 (MH+).

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

Reference:
Patent; EXELIXIS, INC.; WO2007/44515; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics