Month: May 2021

Synthetic Route of 1161847-36-4, 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. 1161847-36-4, name is 6-Chloroimidazo[1,2-b]pyridazin-8-amine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 13.; Reference for Suzuki conditions: Billingsley and Buchwald, J. Am. Chem. Soc. 2007, 129, 3358-3366. A mixture of 6-chloro-imidazo[l,2-b]pyridazin-8-ylamine (0.048 g, 0.29 mmol), 4-tert- butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (0.169 g, 0.444 mmol), potassium phosphate (0.120 g, 0.567 mmol), 2- dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.024 g, 0.058 mmol), palladium acetate (0.007 g, 0.03 mmol), 0.5 mL of n-butanol and 0.2 mL of water in a sealed tube was stirred at 100 0C for 2 d. The resulting cloudy orange mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water, and the aqueous layer was extracted with 5 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to an orange oil. Column chromatography (60 -> 100% EtOAc/hexanes) afforded 0.026 g (23%) of N-[3-(8-amino-imidazo[l,2-b]pyridazin-6-yl)-2-methyl- phenyl] -4-tert-butyl-benzamide 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, 6-Chloroimidazo[1,2-b]pyridazin-8-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/77334; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 69411-05-8, 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows.

11636] 3-Chloro-5-trifluoromethylaniline (517, 3.66 g,18.7 mmol) was dissolved in 70 mE THF and stirred in an ice bath. To it were added 13oC2O (4.48 g, 20.6 mmol) and DMAP (2.51 g, 20.6 mmol). The mixture was stirred for overnight, and was concentrated in vacuo. The residue was taken into 200 mE EtOAc, washed with water x3, dried, rotavaped, and subjected to silica flash colunm using 1% MeOR in DCM to get tert-butyl 3-chloro-5-(trifluoromethyl) phenylcarbamate (518, 3.37 g, 61%) as a white solid. It was dissolved in 100 mE dry THF and treated with NaR (60% in mineral oil, 910 mg, 22.8 mmol) at RT for 15 mm and then iodomethane (1.42 mE, 22.8 mmol) was added. The mixture was stirred for overnight, concentrated, taken into 200 mE EtOAc, washed with water x2, dried, concentrated, and subjected to silica flash column using 0 to 5% EtOAc in DCM to isolate the methylation product as an oil. It was treated with 1:1 TFADCM (10 mE/i 0 mE) at RT for 3 hours, concentrated in vacuo, taken into 200 mE EtAOc and 50 mE iN NaOH. The organic phase was separated, washed with water, dried, subjected to silica flash column with 1% MeOR in DCM to isolate 3-chioro-N-methyl-5-(trifluoromethyl) aniline (519, 1.76 g, 53%) as an oil.

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-5-trifluoromethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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-Bromo-1-chloro-4-(trifluoromethyl)benzene

EXAMPLE 6; [5-(3-{4-[2-Chloro-5-(trifluoromethyl)phenyllpiperazin-l-yl|isoxazol-5-yl)-2//-tetrazol-2- yl] acetic acid; Step 1 : tert-Butyl 4-r2-chloro-5-(trifluoromethyl)phenyllpiperazine-l-carboxylate; Into a 50 mL pressure vial equipped with a magnetic stir bar was added tert-butyl piperazine-1-carboxylate (2.00 g, 10.7 mmol), palladium(II) acetate (0.24 g, 1.07 mmol) and racemic-BTNAP (1.34 g, 2.15 mmol). The vial was evacuated under vacuum (1 mm Hg) and backfilled with N2 (repeated 3 times). Toluene (10 mL) and 3-bromo-4-chlorobenzotrifluoride (3.06 g, 11.8 mmol) were added to the vial and the solvent was degassed for 10 min with a steady flow of nitrogen before being heated to 120 0C for 16 h. The reaction mixture was filtered through a plug of celite on a sintered glass funnel, washing with diethyl ether (100 mL). The filtrate was concentrated and purified by column chromatography through silica gel, eluting with 0% EtOAc in hexanes to 40% EtOAc in hexanes as a gradient. The desired product was obtained as a light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 454-78-4, its application will become more common.

Reference:
Patent; MERCK FROSST CANADA LTD.; ISABEL, Elise; LACHANCE, Nicolas; LECLERC, Jean-Philippe; LEGER, Serge; OBALLA, Renata, M.; POWELL, David; RAMTOHUL, Yeeman, K.; ROY, Patrick; TRANMER, Geoffrey, K.; ASPIOTIS, Renee; LI, Lianhai; MARTINS, Evelyn; WO2010/94126; (2010); 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. 87-63-8, name is 2-Chloro-6-methylaniline, A new synthetic method of this compound is introduced below., name: 2-Chloro-6-methylaniline

To a cold stirring solution of 2-chloro-6-methylaniline (59.5 g 0.42 mol) and pyridine (68 ml, 0.63 mol) in THF (600 mL) was added 3-ethoxyacryloyl chloride (84.7 g, 0.63 mol) slowly keeping the temp at 0-5C. The mixture was then warmed and stirred for 2 h. at 20C. Hydrochloric acid (1N, 115 mL) was added at 0-10C. The mixture was diluted with water (310 mL) and the resulting solution was concentrated under vacuum to a thick slurry. The slurry was diluted with toluene (275 mL) and stirred for 15 min. at 20-22C then 1 h. at 0C. The solid was collected by vacuum filtration, washed with water (2 x 75 mL) and dried to give 74.1 g (73.6 % yield) of (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide). lH NMR (400 Hz, DMSO-d6) 8 1. 26 (t, 3H, J= 7 Hz), 2.15 (s, 3H), 3.94 (q, 2H, J= 7 Hz), 5.58 (d, 1H, J=12.4 Hz), 7.10-7. 27 (m, 2H, J=7.5 Hz), 7.27-7. 37 (d, 1H, J=7.5 Hz), 7.45 (d, 1H, J=12.4 Hz), 9. 28 (s, 1H) ; l3c NMR (100MHz, CDC13) b : 14. 57, 18.96, 67.17, 97.99, 126. 80, 127. 44, 129. 07, 131.32, 132.89, 138. 25,161. 09,165. 36.

The synthetic route of 87-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/77945; (2005); A2;,
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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 69411-05-8

11568] 3-Chloro-5-trifluoromethylaniline (3.66 g, 18.7 mmol) was dissolved in 70 mE THF and stirred in an ice bath. To it were added 13oC2O (4.48 g, 20.6 mmol) and DMAP (2.51 g, 20.6 mmol). The mixture was stirred for overnight, and was concentrated in vacuo. The residue was taken into 200 mE EtOAc, washed with water x3, dried, rotavaped, and subjected to silica flash column using 1% MeOH in DCM to get tert-butyl 3-chloro-5-(trifluoromethyl)phenylcarbamate (466,3.37 g, 61%) as awhite solid. It was dissolved in 100 mE dry THF and treated with NaH (60% in mineral oil, 910 mg, 22.8 mmol) at RT for 15 mm and then iodomethane (1.42 mE,22.8 mmol) was added. The mixture was stirred for overnight, concentrated, taken into 200 mE EtOAc, washed with water x2, dried, concentrated, and subjected to silica flash colunm using 0 to 5% EtOAc in DCM to isolate the methylation product as an oil. It was treated with 1:1 TFADCM (10 mE/lO mE) at RT for 3 hours, concentrated in vacuo, taken into 200 mE EtAOc and SOmE iN NaOH. The organic phase was separated, washed with water, dried, subjected to silica flash column with 1% MeOH in DCM to isolate 3-chloro-N- methyl-5-(trifluoromethyl)aniline (467, 1.76 g, 53%) as an oil.

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; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 928-50-7,Some common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, molecular formula is C5H9Cl, 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: Sodium azide (0.5 g, 8 mmol) was added to the stirredsolution of chlorides 1b,e,f or tosylates 1c,d (6 mmol) indry DMSO (8 ml) at room temperature. The reactionmixture was stirred at 70C for 15 h, then washed well withwater (3×10 ml) and extracted with CH2Cl2 (2×10 ml). Combined organic layers were dried over MgSO4, filtered,and concentrated to obtain the crude azides 2b-f. Resultingazides were dissolved in Et2O (10 ml), PPh3 (1.6 g, 6 mmol)was added, the reaction mixture was stirred at 0C for 1.5 h.Then water (1 ml) was added and the reaction mixture wasstirred at room temperature overnight. After the completion,the reaction mixture was poured onto crushed ice andextracted with CH2Cl2 (3×10 ml). Organic layers werecombined and dried over MgSO4, filtered, and concentratedunder reduced pressure to obtain amines 3b-f. Solution ofamine 3a-f in CH2Cl2 (10 ml) was stirred with K2CO3(2.2 g, 16 mmol) at 0C for 15 min. Acryloyl chloride(0.6 ml, 7 mmol) was added dropwise at 0C, and themixture was stirred at room temperature for 6 h. Thereaction was monitored by TLC. After completion of thereaction, cold water (10 ml) was added and the mixture wasextracted with CH2Cl2 (3×10 ml). The combined organiclayers were washed with brine, dried over anhydrous MgSO4,filtered, and concentrated under reduced pressure. Thecrude diene amides 4a-f were purified on silica gel column,eluting with EtOAc-petroleum ether with increasing gradient.

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

Reference:
Article; Gondal, Humaira Yasmeen; Buisson, Didier; Chemistry of Heterocyclic Compounds; vol. 52; 3; (2016); p. 183 – 191; Khim. Geterotsikl. Soedin.; vol. 52; 3; (2016); p. 183 – 191,9;,
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 120758-03-4 as follows. Safety of 2-Chloro-3,5-dimethoxyaniline

Example 14 Synthesis of 1-(2-chloro-3,5-dimethoxyphenyl)-2-cyclohexyl-6-cyclopentyl-3-methyl-4(1H)-pyridinone (Compound 81) In 150 ml of chlorobenzene were dissolved 4.5 g of 1-cyclohexyl-5-cyclopentyl-2-methyl-1,3,5-pentanetrione and 6.0 g of 2-chloro-3,5-dimethoxyaniline. To the mixture was added 2.0 g of titanium tetrachloride, followed by refluxing for 4 hours. The chlorobenzene of the reaction mixture was distilled off and the residue was extracted with 150 ml of chloroform. The organic layer was washed first with 100 ml of 10% hydrochloric acid and then with 100 ml of a 10% aqueous solution of sodium hydroxide. After washing the organic layer with water, it was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by column chromatography on silica gel (eluent: chloroform). The resulting crystals were recrystallized from ethyl acetate, affording 0.6 g of 1-(2-chloro-3,5-dimethoxyphenyl)-2-cyclohexyl-6-cyclopentyl-3-methyl-4(1H)-pyridinone having a melting point of 230-231 C.

According to the analysis of related databases, 120758-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP304057; (1989); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 54730-35-7,Some common heterocyclic compound, 54730-35-7, name is 3,5-Dichloro-4-methylaniline, molecular formula is C7H7Cl2N, 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 3,5-dichloro-4-methylaniline (0.9 mmol, 157.5 mg) in dimethyl sulfoxide (3.0 mL) is added carbodiimidazole (1.1 mmol, 178.4 mg) and stirred at room temperature for 2 hours. did.Then, 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.0 mmol, 319.0 mg) and triethylamino(1.0 mL) was added and stirred at room temperature for 24 hours. After heating under reduced pressure and distilling off the solvent, the resulting solid was dissolved in ethyl acetate (300 mL) and extracted three times with a saturated aqueous ammonium chloride solution (100 mL).The organic layers are combined and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure.It was. The resulting solid was washed with toluene and ethyl acetate, dissolved in methanol, and subjected to silica gel column chromatography (ethyl acetate: methanol = 1: 1) to give UA-44 (12.0 mg, yield 3%). Was obtained as a white solid.

The synthetic route of 54730-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
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. 10541-69-2, name is (2,5-Dichlorophenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (2,5-Dichlorophenyl)methanamine

In a 20 mL scintillation vial, 4-amino-5-cyano-6-ethoxy-pyrindine-2-carboxylic acid (19 mg, 0.09 mmol) was dissolved in DMA (0.7 mL). Then TBTU (30 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added, followed by the addition of 2,5-dichlorobenzylamine (18 mg, 0.11 mmol, 1.2 eq.) in DMA (0.6 mL). Then TEA (9.37 mg, 0.09 mmol) dissolved in DMA (0.7 mL) was added. The mixture was shaken at room temperature for 24 hours. The crude mixture was purified using reverse phase HPLC (TFA). 1H NMR (500 MHz, DMSO-D6/D2O) ? ppm 1.24 (t, 3H) 4.03-4.86 (m, 4H) 5.88-7.87 (m, 4H). MS (ESI) positive ion 365 (M+H)+; negative ion 363(M?H)?.

The synthetic route of 10541-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1009102-44-6,Some common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, molecular formula is C9H11Cl2N, 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.

Step 2:To a solution of methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)- 1 ,3,5-triazin-2- ylamino)benzoate (870 mg, 2.4 mmol) from Step 1 in THF (10 mL) was added l-(4- chlorophenyl)cyclopropanamine, HC1 (500 mg, 2,450 mmol) and Hunig’sBase (1.677 mL, 9.60 mmol). The resulting mixture was stiiTed for 16 h. The precipitate was filtrated through a plug washing with THF to give acrude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.1 g of the desired product as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; MULL, Eric; ZHAO, Qian; WANG, Tao; ZHANG, Zhongxing; SCOLA, Paul Michael; WO2012/24373; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics