Author: Jessica.F

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. SDS of cas: 918538-05-3

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).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

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;,
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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. 622-86-6, name is (2-Chloroethoxy)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: (2-Chloroethoxy)benzene

2-(4-Chlorophenyl)butanoic acid (397.3 mg, 2.0mmol) was suspended with stirring in trifluoroacetic anhydride (277.4 uL, 2.0mmol). Then (2-chloroethoxy)benzene (252.4 uL, 1.8 mmol) was added dropwise andthe resulting mixture was stirred at room temperature overnight. The reactionwas quenched with saturated sodium bicarbonate solution (5 mL) and extractedwith ethyl acetate (2 x 15 mL). Thecombined organic layers were dried over anhydrous magnesium sulfate andconcentrated on a rotary evaporator. Theresulting residue was purified by reverse-phased chromatography (C-10 column,gradient of acetonitrile in water with 0.1% trifluoroacetic acid) to afford297.1 mg (49%) of the desired product as a yellow solid. 1H NMR (400 MHz, MeOD) delta 7.99 (d,J = 8.9 Hz, 2H), 7.28 (m, 4H), 6.96 (d, J = 8.9 Hz, 2H), 4.58 (t, J = 7.2Hz,1H), 4.27 (t, J = 5.5 Hz, 2H), 3.84 (t, J = 5.5 Hz, 2H), 2.11 (m, 1H), 1.78(m, 1H), 0.88 (t, J = 7.3 Hz 3H); MS (ESI) (m/z) 318.1/320.1 (M+H)+.

The synthetic route of 622-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Childers, Wayne; Fan, Rong; Martinez, Rogelio; Colussi, Dennis J.; Melenski, Edward; Liu, Yuxiao; Gordon, John; Abou-Gharbia, Magid; Jacobson, Marlene A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
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Electric Literature of 4535-90-4, 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. 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 30 trans-(2-{8-Chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulen-5-yl}-ethyl)-methyl-amine A mixture of trans-8-chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.130 mmol), cesium carbonate (170 mg, 0.521 mmol) and 2-methylaminoethyl chloride hydrochloride (67.7 mg, 0.521 mmol) in acetonitrile (1.3 ml) was heated at 70 C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between 1 M aqueous sodium hydroxide solution (2 ml) and ethyl acetate (5 ml). The layers were separated. The aqueous layer was extracted with three 5-ml portions of ethyl acetate. The combined organic layers were concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the hydroformate salt of the title compound, which was liberated by filtration over aminopropyl modified silica gel (10 g) with methanol (20 ml) as eluent. The filtrate was concentrated to dryness. The residue was redissolved in ethyl acetate, filtrated over cotton wool and concentrated to dryness to give the title compound (38 mg, 66%) as off-white solid. MS m/e: 441 ([M+H]+).

The synthetic route of 2-Chloro-N-methylethanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dolente, Cosimo; Schnider, Patrick; US2011/275801; (2011); A1;,
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Application of 1939-99-7, These common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl chloride, 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.

Preparation 19: 3-Phenyl-l ,4,5-oxathiazepane 4,4-dioxide Step 1 : A/-(2-((Tert-butyldimethylsilyl)oxy)ethyl)- 1 -phenylmethanesulfonamide To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0 C was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel solumn chromatography (0-30% Acetone in heptane, 216 nM) to A^-(2-((tert-butyldimethylsilyl)oxy)ethyl)-l-phenylmethanesulfonamide (17.8 g, 81 % yield). LCMS (ESI), m/z, 330. [M+H] +.

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; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); A1;,
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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. 29671-92-9, name is Carbamimidic chloride hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of CH4Cl2N2

To a suspension of Ig (400 mg, 0.66 mmol) in methanol (26 mL) was dropwise added concentrated HCl (4.5 mL) while stirring. The mixture was stirred at room temperature for 1 h. The resulting solution was concentrated in vacuo and dried. The residue was then mixed with methyl sulfone (6 g) and chloroamidine hydrochloride (113 mg, 0.99 mmol) in a microwave vial, and heated at 150 0C for 1 h. While cooling to room temperature, the mixture was treated with IN ammonium hydroxide (5 mL) and ethyl acetate (5 mL) with vigorous stirring. The organic layer was concentrated and the residue was purified by silica gel column chromatography (EtOAc / hexanes), affording 3a as an oil (0.05 g, 13%). MS = 584.0 (M+ H+). 1H NMR (300 MHz, CDCl3): B 8.09 (s, IH), 7.2-7.4 (m, 15H), 5.33 (s, IH), 4.4-4.8 (m, 7H), 3.96 (m, IH), 3.86 (m, 2H), 1.16 (s, 3H).

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.; BUTLER, Thomas; CHO, Aesop; KIM, Choung, U.; XU, Jie; WO2010/93608; (2010); A1;,
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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. 363-51-9, name is 2-Chloro-6-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Chloro-6-fluoroaniline

A stirred solution of 9 4-hydroxy-2-methylsulfanyl-pyrimidine-5-carboxylic acid (5.70 g, 30.65 mmol, 1.0 eq) and 237 2-chloro-6-fluoro-aniline (4.50 g, 30.65 mmol, 1.0 eq) in 24 toluene (200 mL) was purged with nitrogen gas for 15 min. To the above solution 91 PCl3 (30 mL) was added. The reaction was heated at 100 C. for 72 h. Progress of reaction was monitored by LCMS. After completion of reaction, solvent was removed under reduced pressure, residue was diluted with a mixture of 238 diethyl ether: 30 MeOH (10:1) (100 mL) stirred for 15 min then filtered off. Solid was suspended in MeOH (20 mL), stirred for 5 min, filtered off and washed with MeOH (10 mL), and then dried under vacuum to obtain of 239 N-(2-chloro-6-fluoro-phenyl)-4-hydroxy-2-methylsulfanyl-pyrimidine-5-carboxamide (5.0 g, 52.8%). (0370) LCMS: 314 [M+1]+

The synthetic route of 363-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; KUMAR, Varun; (360 pag.)US2019/106436; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 93-50-5, name is 4-Chloro-2-methoxyaniline, 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 93-50-5, SDS of cas: 93-50-5

To a solution of 4-chloro-2-methoxy-phenylamine (600 mg, 3.81 mmol) in ethanol (12 ml) at 50C was added a solution of silver sulphate (2.14 g, 6.85 mmol) and iodine (967 mg, 3.81 mmol) in ethanol (8 ml). The resulting reaction mixture was stirred at 50C for 4h. After cooling at 25C, reaction mixture was filtered through a bed of celite and the filtrate was diluted with EtOAc (30 ml). The organic phase was washed with aqueous Na2S203 solution (2×15 ml), and brine (10 ml), dried over anhydrous Na2S04, filtered, and evaporated off in vacuo. The crude residue was purified by flash column chromatography (2% EtOAc in hexane) to afford 4-chloro-2-iodo-6-methoxy-phenylamine (160mg, 15%) as brown sticky liquid. GC-MS: 283 (M).

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; F. HOFFMANN-LA ROCHE AG; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RUDOLPH, Markus; WO2013/64465; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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 33863-76-2, COA of Formula: C6H3BrClF

A solution of 1-bromo-3-chloro-5-fluorobenzene (50.0 g, 239 mmol) in DMF (300 ml.) was treated with sodium methoxide (15.5 g, 286 mmol) and the reaction was stirred overnight at rt. The mixture was diluted with ethyl acetate (500 ml.) and washed with water (700 ml_). The organic layer was isolated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give 51.0 g of the title compound which was used without purification. 1H NMR (DMSOd6) ¡ì 7.23 (t, 1 H), 7.13 – 7.15 (m, 1 H), 7.05 (t, 1 H), 3.77 (s, 3 H).

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; SMITHKLINE BEECHAM CORPORATION; WO2008/157330; (2008); A1;,
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Application of 622-24-2, 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 622-24-2 as follows.

To the reaction flask was added substances five, six substances, dimethylformamide, potassium carbonate, the reaction was cooled to 25 , the reaction mixture was added to ice water, ice-water is 10 times the mass of the reaction liquid was filtered, washed with water, Dry matter seven. The molar ratio of the substance five, substance six, potassium carbonate and dimethylformamide was 1: 1: 1: 10, and the temperature was raised to 80 C for 4 hours

According to the analysis of related databases, 622-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHINA THREE GORGES UNIVERSITY; TAN, XIAO; LIU, SEN; YANG, LITING; (22 pag.)CN106243058; (2016); A;,
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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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., SDS of cas: 63624-28-2

B) 5-Chloro-3-(2-isopropoxyphenyl)-1-[(2,4-dimethoxyphenyl)sulphonyl]-3-[2-oxo-2-[4-(4-pyridyl)-1-piperazinyl]ethyl]-1,3-dihydro-2H-indol-2-one, laevorotatory isomer. 0.025 g of 60% sodium hydride in oil is added to a mixture of 0.3 g of the compound obtained in the preceding step in 10 ml of THF, and the mixture is stirred at 20 C. for 15 minutes. 0.19 g of 2,4-dimethoxybenzenesulphonyl chloride is then added and the mixture is stirred at 20 C. for 2 hours.The reaction mixture is concentrated under vacuum, the residue is taken up in water and extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum.The residue is chromatographed on silica gel, eluding with DCM and then with acetone. 0.1 g of the expected product is obtained. 1H NMR: DMSO-d6: delta (ppm): 0.6: d: 3H; 1.2: d: 3H; 3.0 to 4.0: m+2s: 16H; 4.6: mt: 1H; 6.4 to 7.2: mt: 9H; 7.4: bd: 1H; 7.7: dd: 2H; 8.1: d: 2H.

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; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); A1;,
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