Month: July 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Step (2) : Preparation of 1, 3-benzodioxol-5-ylmethvl methyl sulfone 9.7 g of 5- (chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetraliydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C, and reacted for 10 minutes. The reactant was then heated to 50C and reacted for 1 hour. The reaction mixture was cooled to 0C and then slowly added to a flask containing [1, 3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 5 ml methane sulfonyl chloride, the mixture was reacted for 30 minutes, and the reactant was heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column cluomatography using ethyl acetate: n-hexane (1: 3), to give 0.75 g of the title compound of the following formula la (Rf: 0.35, Yield: 5%). [Chemical Formula 1 a] The compound was dissolved in CDC13 and TMS and then characterized by’H NMR spectroscopy. The result is as follows; ‘H NMR 6 : 2.75 (s, 3H), 4.14 (s, 2H), 5.97 (s, 2H), 6.81-6. 88 (m, 3H).

The synthetic route of 20850-43-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
Chloride – Wikipedia,
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Synthetic Route of 39226-95-4, These common heterocyclic compound, 39226-95-4, name is 2,3-Dichlorobenzylamine, 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.

EXAMPLE 260 N-(2,3-dichlorobenzyl)-2-(5-isoquinolinyl)propanamide The title compound was prepared using the procedure described in Example 222B using 2,3-dichlorobenzylamine and 2-(5-isoquinolinyl)propanoic acid instead of 4-(trifluoromethoxy)benzylamine and 5-isoquinolinylacetic acid. MS (ESI+) m/z 359 (M+H)+; MS (ESI-) m/z 357 (M-H)-; 1H NMR (DMSO, 300 MHz) delta 1.54 (d, J 7.1, 3H), 4.20 (m, 2H), 4.53 (q, J 7.1, 1H), 7.17 (d, J 7.8, 1H), 7.26 (t, J 7.8, 1H), 7.52 (d, J 8.1, 1H), 7.78 (t, J 7.8, 1H), 7.91 (d, J 6.5, 1H), 8.16 (d, J 8.1, 1H), 8.24 (d, J 6.4, 1H), 8.59 (d, J 6.2, 1H), 8.66 (t, J 5.8, 1H), 9.50 (s, 1H).

The synthetic route of 39226-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); A1;,
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These common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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. Quality Control of 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline

To a solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (500 mg, 2.46 mmol) and 3-amino-5-cyclopropylpyrazole (303 mg, 2.46 mmol) in DMF (10 mL) is added triethylamine (0.357 mL, 2.56 mmol) followed by sodium iodide (368 mg, 2.46 mmol) and the reaction mixture is heated at 90 C. for 20 h. The reaction mixture is partitioned between ethyl acetate and aqueous saturated NaHCO3. The organic layer is washed with brine and evaporated in vacuo. The residue is purified by flash chromatography (SiO2, hexane/AcOEt gradient) to give (2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine.

The synthetic route of 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bebbington, David; Charrier, Jean-Damien; Golec, Julian; Miller, Andrew; Knegtel, Ronald; US2005/38023; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, 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 72235-58-6, Application In Synthesis of (4-Chloro-3-fluorophenyl)methanamine

A mixture of Example 477A (61.7 mg, 0.128 mmol), (4-chloro-3- fluorophenyl)methanamine (0.019 mL, 0.153 mmol), and triethylamine (0.021 mL, 0.153 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 50 C for 3 hrs. After cooling, the reaction mixture was treated with brine and extracted with ethyl acetate (2x). The combined organic layers were dried over MgSO/t, filtered, and concentrated. The residue was purified by reverse- phase HPLC (see protocol in Example 112D) to provide the title compound (23.7 mg, 35%).JH NMR (400 MHz, DMSO-<) delta ppm 7.50 (dt, J = 14.5, 8.4 Hz, 2H), 7.26 - 7.15 (m, 2H), 7.11 - 7.00 (m, 2H), 6.83 (ddd, J = 8.9, 2.8, 1.1 Hz, 1H), 6.18 (t, J = 6.1 Hz, 1H), 5.74 (s, 1H), 5.02 (d, J = 4.4 Hz, 1H), 4.46 (s, 2H), 4.14 (d, J = 6.1 Hz, 2H), 4.01 (dt, J = 8.5, 3.8 Hz, 1H), 2.23 (ddd, J = 12.6, 9.4, 2.8 Hz, 1H), 2.12 - 1.98 (m, 1H), 1.95 - 1.63 (m, 8H); MS (ESI+) m/z 528.2 (M+H)+. 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, (4-Chloro-3-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 220227-21-4, 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 220227-21-4 as follows.

Into a 100-mL round-bottom flask, were placed 3-(chloromethyl)-1 ,2,4-thiadiazol-5-amine (1 .00 g, 6.68 mmol, 1 .00 equiv), N,N-dimethylformamide (30 m L), sodium hydride (242 mg, 10.08 mmol, 1 .50 equiv), 2,4,5-trifluorobenzene-1 -sulfonyl chloride (1 .85 g, 8.02 mmol, 1 .00 equiv). The resulting solution was stirred for 1 .5 h at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the organic layers combined. The resulting mixture was washed with brine, dried and concentrated under vacumm. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :6). This resulted in 700 mg (30%) of N-[3- (chloromethyl)-l ,2, 4-thiadiazol-5-yl]-2, 4, 5-trifluorobenzene-1 -sulfonamide as a yellow solid.

According to the analysis of related databases, 220227-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZALICUS PHARMACEUTICALS, LTD.; SHORT, Glenn, F., III; ROMERO, Donna, L.; LEE, Margaret, S.; WO2015/130957; (2015); 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 6775-78-6 as follows. category: chlorides-buliding-blocks

In a 500 ml single-necked round bottom flask was added3-Amino-6-chloropyridazine(38.86 g, 300 mmol), 40% aqueous chloroacetaldehyde (58.88 g, 300 mmol), sodium bicarbonate (30.24 g, 360 mmol) and 260 mLTert-butanol, start magnetic stirrer, the reaction flask was stirred at 80 C for 7 hours.TLC detection of raw materials 3-amino-6-chloropyridazine reaction is completed,Nitric acid (22.68 g, 360 mmol) was added and reacted for a further 4 hours with stirring.TLC and GC analysis confirmed that the intermediate 6-chloroimidazo [1,2-b] pyridazine was completely reacted. The reaction mixture was suction filtered and the filter cake was recrystallized from ethyl acetate: n-hexane = 1: 3 to give the pure product 3-nitro-6-chloroimidazo [1,2-b] pyridazine. The filtrate was extracted with ethyl acetate , The extract was removed by rotary evaporation to give the crude product, which was recrystallized from ethyl acetate: n-hexane = 1: 3 to obtain the pure product3-nitro-6-chloroimidazo [1,2-b] pyridazine,After drying, the yield was calculated 86.30%, purity 99.31%

According to the analysis of related databases, 6775-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Youbang Biochemical Technology Co., Ltd.; Geng Xuanping; Lai Chao; Lai Ziteng; Lai Xinsheng; (6 pag.)CN106632353; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

[0 144j To a solution of 5 -(aminomethyl)-N-((2-methylthiazol-5 -yl)methyl)pyrazine-2- carboxamide (0.070 g, 0.26 mmol) and 3,5-difluorobenzenesulfonyl chloride (0.056 g, 0.26 mmol) in dichioromethane (2 mL) was added triethylamine (0.1 mL, 0.53 mmol) at 0 C and resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (15 mL x 3). The organic layer was washed with saturated sodium bicarbonate solution (10 mL x 2), brine (20 mL), dried over sodium sulfate and concentrated under vacuum to get the crude material which was purified by preparative HPLC (analytical conditions: column: Xbridge C18 (19 mm X 250 mm X 5 jim), mobile phase (A): 5 mM ammonium acetate in water, mobile phase (B): HPLC grade acetonitrile. Elution gradient: 0-20 mm, 5-95% B in A) to afford the title compound 5-(((3,5- difluorophenyl)sulfonamido)methyl)-N-((2-methylthiazol-5 -yl)methyl)pyrazine-2-carboxamide (0.013 g, 12% yield) as an off-white solid. Calculated M+H: 440.06; Found M+H: 440.13.

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

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 19230-27-4, A common heterocyclic compound, 19230-27-4, name is 1,3-Dibromo-2-chlorobenzene, molecular formula is C6H3Br2Cl, 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 1,3-dibromo-2-chlorobenzene (1.47 g, 5.45 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (800 mg, 3.64 mmol), Pd(dppf)C12CH2C12 (297 mg, 0.36mmol) and potassium carbonate (1.005 g, 7.27 mmol) under N2 was added a mixture of solvents (12 mL and 3 mL water) and heated to 85 C for 2h. After cooling to room temperature, the reaction was dilutedwith CH2C12 and water. The organic layer was separated, dried with Na2504 and concentrated. The residue was purified by silica gel chromatography (eluting with 5% to 40% EtOAc-Hex) to give 3?- bromo-2?-chloro- [1,1 ?-biphenyll -4-ol.

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; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 7006-52-2, 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 7006-52-2 as follows.

Sodium hydride (4.89 g, 73.4 mmol, 60percent in oil) was added portionwise to an ice-cooled solution of N-methyl-3-chloroaniline (8 g, 56.5 mmol) in DMF (40 ml). This mixture was5 then added to an ice-cooled solution of 2,4-dichloropyrimidine (16.8 g, 113 mmol) in DMF (40 ml). The resulting mixture was heated at 700C for 18 hrs. Additional sodium hydride (large excess) was added and the mixture was heated at 1000C for 2 hrs.. After cooling, the mixture was poured in saturated aqueous sodium bicarbonate and extracted with DCM. The organic layer was dried over magnesium sulfate and filtered. After evaporation of the o solvents, the residue was purified by chromatography on silica gel (eluant: 0 to 20percent EtOAc in DCM, then 10percent methanol in EtOAc ) to give 4-[(3-chlorophenyl)-methyl- ammo]-lH-pyrimidin-2-one as a light brown solid (4 g, 30percent). NMR Spectrum: (DMSOd6 and CF3CO2D) 3.53 (s, 3H), 7.46 (m, IH), 7.67-7.60 (m, 3H), 7.78 (m, IH); Mass spectrum: MH+ 236

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/104754; (2008); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-2-fluoroaniline

General procedure: N,N-Carbonyldiimidazole (0.17 g, 1.2 mmo1) was added to a solution of 8 (0.21 g, 1 mmo1) in anhydrous tetrahydrofuran (THF) and the mixture was stirred for 10 min at room temperature under a nitrogen atmosphere. Subsequently, substituted aniline or phenylethylamine (1.2 mmol) was slowly added to the mixture. The mixture was stirred at 80 oC overnight, then filtrated. The filtrate was evaporated under reduced pressure to give an oil or colored solid, which was purified by column chromatography with petroleum ether/ethyl acetate (7 : 1) to obtain the desired product 9a-9g.

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:
Article; Liu, Yang; Li, Yijing; Liu, Jianzhen; Yang, Limin; Li, Pengzhan; Zhao, Guisen; Letters in drug design and discovery; vol. 13; 4; (2016); p. 314 – 323;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics