Tag: M.W=100-200

Reference of 7051-16-3,Some common heterocyclic compound, 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, molecular formula is C8H9ClO2, 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 1-chloro-3,5-dimethoxybenzene (5 g, 29.0 mmol) and TMEDA (4.37 mL, 29.0 mmol) in diethyl ether (100 mL, 962 mmol) at -78 C under N2 atmosphere was charged with BuLi (19.91 mL, 31.9 mmol) dropwise over a period of 30 minutes using a syringe pump. After stirring for 4 hours at -78 C, DMF was added and the reaction mixture continued to stir for 1.5 hours after which 1N HCl (~30 mL) was added (all at -78 C). The reaction mixture was warmed to room temperature and extracted withy ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The residue was purified by ISCO using hexanes/EtOAc as eluent. Fractions containing the desired product were concentrated to dryness to give the title material (1.97 g, 9.82 mmol, 33.9% yield) as a light yellow solid. LC (Method B): 1.924 min. LCMS (APCI): calcd for C9H10ClO3 [M+H]+ m/z 201.03, found 201.0. 1H NMR (CDCl3, 400 MHz): delta ppm 10.28 (s, 1H), 6.87 (s, 2H), 3.86 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne; WO2013/163241; (2013); A1;,
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Electric Literature of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step B4-bromo-6-( 1, 1-dimethylethyl)-2-(trichloromethyl)- 1H-benzimidazole[00244] 3-bromo-5-(1 ,1-dimethylethyl)-1 ,2-benzenediamine (1.2 g, 4.9 mmol) was dissolved in acetic acid (25 mL) and methyl 2,2,2-trichloromethylacetimidatate (0.94 mL, 7.4 mmol) was added drop-wise. The reaction was stirred for 3 hours. The mixture was diluted with ethyl ether and washed with water. The aqueous layer was extracted again with ether. The combined organic layers were washed with water, washed with brine, dried over sodium sulfate, and concentrated to give the title compound (0.91 g, 50%). LCMS: m/z 369, 371 , 373 (M+1).

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 39989-43-0, name is 3,5-Dichlorobenzylamine, 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 39989-43-0, Recommanded Product: 39989-43-0

EXAMPLE 125 8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid 4-fluoro-benzylamide (125) In a manner similar to that for the compound 124H in Example 124, Step 8, substituting 3,5-dichlorobenzylamine with 4-fluorobenzylamine in Step 8, 8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic acid the 4-fluoro-benzylamide (125) was prepared. 1H NMR (400 MHz, CD3OD) delta 9.10 (d, 1H), 8.72 (d, 1H), 7.84 (dd, 1H), 7.43 (dd, 2H), 7.06 (t, 2H), 4.64 (s, 2H), 2.88 (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; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); A1;,
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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 622-86-6 as follows. Application In Synthesis of (2-Chloroethoxy)benzene

To a stirred solution of l-(2-chloroethoxy)benzene (48 g, 1.0 eq) in 400 mL CH2CI2 at 0 C was added dropwise a solution of 4-methoxybenzoyl chloride (62 g, 1.2 eq) and AICI3 (49 g, 1.2 eq) in 400 mL CH2CI2 while maintaining the temperature at 0 C. After the addition, the reaction was stirred at rt for 1 h. Then added ice water to quench the reaction and extracted with CH2CI2. The extract was washed with brine, dried and evaporated in vacuo. Hexane (500 mL) was added to the residue, cooled to 0 C and stirred for 30 min, then filtered and washed with cold hexane and dried to give the product as a white solid (85 g, 96%). NMR (400 MHz, CDC13) 67.79 (dd, J = 6.8 Hz, 2.0 Hz, 4H), 6.97 (dd, J = 8.8 Hz, 2.0 Hz, 4H), 4.32 (t, J = 6.0 Hz, 2H), 3.89 (s, 3H), 3.86 (t, J = 6.0 Hz, 2H).

According to the analysis of related databases, 622-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Li; HU, Yuandong; YU, Rong; HU, Wei; ZHAO, Na; PENG, Yong; LUO, Hong; HAN, Yongxin; WO2013/97773; (2013); A1;,
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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 367-22-6 as follows. Recommanded Product: 4-Chloro-3-fluoroaniline

Into a 500-mL round-bottom flask was placed 4-chloro-3-fluoroaniline (5.08 g, 34.9 mmol), ACN (200 mL), and NBS (18.69 g, 105.0 mmol). The resulting solution was stirred for 12 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :200 to 1 : 100). This resulted in 9.7 g (92%) of the title compound as a light yellow solid. MS-ESI: 303.8/305.8/301.8 (M+l).

According to the analysis of related databases, 367-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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Related Products of 4090-55-5,Some common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, molecular formula is C5H10ClO3P, 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.

General procedure: Ph(But)P(O)Cl or 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (5.0mmol) was added to the suspension of NaH (0.133g, 5.5mmol) in THF (25mL). Subsequently, 5,7-dibromo-2-methylquinolin-8-ol (1a), 5-fluoro-2-methylquinolin-8-ol (1i) (5.0mmol) in THF (5mL), was added. The reaction was carried out for 24 h under reflux. The mixture was allowed to cool to room temperature. The reaction was neutralized with aqueous solution of KHSO4. After extraction with CH2Cl2 (3×50mL), the organic phase was dried over MgSO4, followed by filtration and solvent evaporation. The crude product was purified by chromatography and crystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, its application will become more common.

Reference:
Article; Nycz, Jacek E.; Szala, Marcin; Malecki, Grzegorz J.; Nowak, Maria; Kusz, Joachim; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 351 – 359;,
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Adding a certain compound to certain chemical reactions, such as: 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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 918538-05-3, Quality Control of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

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-Dichloropyrrolo[2,1-f][1,2,4]triazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 39989-43-0, name is 3,5-Dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H7Cl2N

Dichlorobenzylamine (117 mg) was added to a solution of intermediate 36 (180 mg) in drydichloroethane (5 mL) under a Nitrogen atmosphere. After stirring for 1 h at r. t. NaBH (OAc) 3 (169 mg) was added and the resulting mixture was stirred at r. t. overnight. Then it was diluted with DCM, washed with an aqueous saturated sodium hydrogen carbonate solution, dried and concentrated in vacuo to give a crude oil, which was purified by flash chromatography (Biotage Flash 25M, CH/AcOEt 4: 1). The two fractions corresponding to products with Rf=0.36 and Rf=0.50 (CH/AcOEt 1: 1, detection with ninhydrine) were collected to give, after evaporation, an oil (40 mg) which was then dissolved, under a Nitrogen atmosphere, in dry MeOH (5 mL) and to which sodium methoxide (4.5 mg) was added. The mixture was refluxed for 5 h, then it was allowed to cool to r. t. and solvent was removed in vacuo. The residue was dissolved in AcOEt, washed with an aqueous saturated sodium hydrogen carbonate solution, dried and concentrated in vacuo. The crude product thus obtained was purified by flash chromatography (CH/AcOEt 9: 1) to give the title compound (35 mg) as a colourless oil. T. I. c.: CH/AcOEt 1: 1, Rf=0.5 (detection with ninhydrine). NMR(CDCI3) :6 (ppm) 7.31 (dd, 2H); 7.2 (t,1H) ; 6.98 (t, 2H); 6.83 (d, 2H); 4.25 (d,1H) ; 4.04 (d, 1H) ; 3.76 (b, 2H); 3.01 (td, 1H) ; 2.88 (m, 1H) ; 2.82 (bm, 1H) ; 2.63 (dd, 1H) ; 2.41 (b, 1H) ; 2.18 (bd, 1H) ; 2.05-2. 15 (m, 2H); 1.94 (b, 1H) ; 1.81 (b, 1H) ; 1.69 (m, 1H) ; 1.4 (s, 9H). MS (ES/+): m/z=543 [M+Na] +.

The synthetic route of 39989-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/49600; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, 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 7781-10-4, Computed Properties of C7H6ClN3

A mixture of (5)-tert-butyl (2,4-dimethyl- 1 -(4-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)pentan-2-yl)carbamate (prepared as described in Example 255, Parts A and B) (99 mg, 0.197 mmol), 4-chloro-7-methyl- 7H-pyrrolo[2,3-dlpyrimidine (synthesis previously described I Med. Chern., 2012,55, 7193) (30 mg, 0.179 mmol), Pd(Ph3P)4 (10.34 mg, 8.95 imol) and 2M aq. solution of potassium phosphate (0.269 mL, 0.537 mmol) in 1,4-dioxane (4 mL) was purged with nitrogen and heated at 100 C for 12h. The reaction mixture was diluted with ethyl acetate (25 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to obtain cmde residue. The residue waspurified by silica gel chromatography (5-10% ethyl acetate in hexanes) to afford (5)- tert-butyl (2,4-dimethyl- 1 -(4-(7-methyl-7H-pyrrolo[2,3-djpyrimidin-4-yl)-2 (trifluoromethyl)phenoxy)pentan-2-yl)carbamate (80 mg, 0.115 mmol, 64% yield) asbrown gummy solid. LCMS (ESI) rn/c 507.3 [(M+H), calcd for C26H33F3N403 507.21; LC/MS retention time (method B): tR = 1.06 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
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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. 6223-78-5, name is 2,5-Dichloro-2,5-dimethylhexane, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H16Cl2

(1) Synthesis of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene (b) The synthesis process is as set forth in the chemical reaction formula below. Into anhydrous toluene (10 mL) were added aluminum chloride (200 mg, 1.5 mmol), 2,5-dichloro-2,5-dimethylhexane (4.70 g, 25.7 mmol) followed by stirring at room temperature for 24 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The yield was 4.90 g (94%). 1H-NMR (500 MHz, CDCl3) delta 7.20 (d, 1H, J=8.0 Hz), 7.10 (d, 1H, J=1.2 Hz), 6.95 (dd, 1H, J=6.5, 1.2 Hz), 2.29 (s, 3H), 1.67 (s, 4H), 1.28 (s, 6H), 1.26 (s, 6H).

The synthetic route of 6223-78-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baba, Masanori; Hashimoto, Yuichi; US2011/172185; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics