Author: Jessica.F

These common heterocyclic compound, 83948-54-3, name is tert-Butyl (5-bromopentyl)carbamate, 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. Formula: C10H20BrNO2

A solution of 4,5-dichlorobenzene-l,2-diamine (350 mg, 1.99 mmol), tert-butyl N-(5-bromopentyl)carbamate (1.05 g, 3.94 mmol), potassium carbonate (819 mg, 5.93 mmol), and sodium iodide (297 mg, 1.99 mmol) in DMF (20 mL) stirred for 18 h at 80 C. The resulting solution was cooled to room temperature, diluted with 50 mL of water, and extracted with 3×40 mL of ethyl acetate. The combined organic phases were washed with 2×30 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography with silica gel (eluting with dichloromethane/methanol (20: 1)) to give tert-butyl 5-(2-amino-4,5-dichlorophenylamino)pentylcarbamate (339 mg, 44%) as brown oil. MS: (ESI, m/z): 362[M+H]+.

The synthetic route of tert-Butyl (5-bromopentyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LEE, Jennifer; BURNETTE, Pearlie; CHELLAPPAN, Srikumar; BARCZAK, Nicholas; CONTI, Chiara; ESCOBEDO, Jaime A.; HAN, Bingsong; LANCIA, David R., Jr.; LIU, Cuixian; MARTIN, Matthew W.; NG, Pui Yee; RUDNITSKAYA, Aleksandra; THOMASON, Jennifer R.; ZHENG, Xiaozhang; (322 pag.)WO2018/75959; (2018); A1;,
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Reference of 445-28-3, A common heterocyclic compound, 445-28-3, name is 2-Fluorobenzamide, molecular formula is C7H6FNO, 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.

General procedure: The appropriate amide 32a-p, benzhydrazide (40a), or p-toluenesulfonylhydrazide (43a) (1.0 mmol, 1.0 equiv) was placed in a SchlenkKjeldahl reaction flask and the flask was evacuated/argon re-filledthree times. Subsequently, anhyd CH2Cl2 (25 mL) was added and themixture was stirred at r.t. for 10 min before dropwise addition of oxalylchloride (3.0 mmol, 3.0 equiv) followed. The reaction mixturewas then stirred at reflux for 2.5-3.0 h before cooling to r.t. and thesolvent was evaporated in vacuo. Subsequently, the appropriate nucleophile32, 34, 36, 38, 40, 42, 43, or 45 (1.1-1.25 mmol, 1.1-1.25equiv) was rapidly added and the flask was evacuated/argon re-filledbefore anhyd toluene (12 mL) was added. The reaction mixture wasthen stirred at reflux for 2.5-3 h before cooling to r.t. and concentrationto about 1/3 of the initial volume on rotavapor. Hexane was addedto the residue and the obtained precipitate (often sonicated) wascollected by filtration under reduced pressure to yield the crudeproduct. When necessary, the isolated material was purified either bycrystallization from MeOH or flash chromatography on silica gel withhexane-EtOAc as the eluent.

The synthetic route of 445-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hernandez, Anolan Garcia; Grooms, Gregory M.; El-Alfy, Abir T.; Stec, Jozef; Synthesis; vol. 49; 10; (2017); p. 2163 – 2176;,
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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. 3144-09-0, name is Methylsulfonamide, A new synthetic method of this compound is introduced below., Product Details of 3144-09-0

General procedure: According to the Scheme 1, 4 mmol of N-(4-Sulfamoylphenyl) acetamide was treated with acetic anhydride (4 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 50C for the predetermined time. The progress of the reaction was monitored by TLC analysis. After the completion of the reaction, the precipitate was collected by filtration and washed with water. The impure precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration to afford N-(4-acetamidophenylsulfonyl)acetamide a1 as the white solid (0.97 g, 95%). The catalytic activities of different heterogeneous catalysts were determined by reactions performed in THF using a 1:1 molar ratio of sulfonamide to acetic anhydride or benzoyl chloride. In a typical route, N-(4-sulfamoylphenyl) acetamide (4 mmol) was treated with acetic anhydride (4 mmol) in the presence of catalyst (0.1 g) in THF (10 mL). After the appropriate time, the catalyst was separated with an external magnetic field, the solvent was evaporated by rotary evaporator. The precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration and was washed with distilled water to afford N-(4-acetamidophenylsulfonyl)acetamide as the white solid (0.95 g, 93%).

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; Ghasemi, Mohammad Hadi; Kowsari, Elaheh; Hosseini, Seyed Kiumars; Tetrahedron Letters; vol. 57; 3; (2016); p. 387 – 391;,
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Application of 1314538-55-0,Some common heterocyclic compound, 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, molecular formula is C6H12BF3KNO2, 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.

[01262] A mixture of 5- [2-chloro-5-(trifluoromethoxy)pyridin-4-yl] -2-(trifluoromethyl)pyrimidine (390 mg, 1.13 mmol, 1.00 equiv), potassium tert-butyl N-[(trifluoroboranuidyl)methyl]carbamate (350 mg, 1.47 mmol, 1.30 equiv), sodium carbonate (359 mg, 3.38 mmol, 2.98 equiv), and Pd(PPh3)2C12 (79 mg, 0.11 mmol, 0.09 equiv) in ethanol (5 mL)/water (0.5 mL) was stirred for 12 hours at 90C under nitrogen. The solid was filtered off. The filtrate was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (2/1) to afford the title compound (200mg, 40%) as a light yellow solid. LCMS [M+H] 439.

The synthetic route of 1314538-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
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Related Products of 885-70-1, 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. 885-70-1, name is 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6 5,11-Dihydro-11-[6-(1-piperidinyl)hexyl]-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-one To a suspension of 33.2 g (0.157 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 875 ml of anhydrous dioxan, 173 ml (approx. 0.45 mol) of a 2.6 molar solution of n-butyl-lithium in n-hexane was added dropwise at ambient temperature and the resulting mixture was then stirred for another hour at the same temperature. It was then heated to 70 C. and at a reaction temperature of not more than 75 C. 83.0 g (0.034 mol) of 1-bromo6-(1-piperidinyl)hexane were added dropwise, then to complete the reaction the mixture was stirred for a further 4 hours at 80 C. After cooling, the solvent was distilled off in a water jet vacuum, the residue was adjusted to pH 7 with dilute aqueous hydrochloric acid and the mixture was then filtered. The filtrate was made alkaline with concentrated aqueous potassium hydroxide solution and extracted exhaustively with dichloromethane. The dichloromethane extracts were dried over sodium sulphate and then evaporated down and the residue remaining was digested with 100 ml of boiling diethyl ether and filtered while hot. The residue remaining after the ether had been removed was purified by chromatography on silica gel (Macherey-Nagel, 0.2-0.5 mm) using dichloromethane/methanol/cyclohexane/ethyl acetate/conc. ammonia 59/7.5/7.5/25/1 (v/v/v/v/v) as eluant. By evaporating the desired fractions and subsequently recrystallising from acetonitrile, a colourless crystalline product with a m.p. of 131 to 132 C. was obtained in a yield of 11.29 g (19% of theory). The hydrochloride melted at 223 C. (ethanol).

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, 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Karl Thomae GmbH; US5006522; (1991); A;,
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Related Products of 956434-30-3,Some common heterocyclic compound, 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, molecular formula is C13H17ClN2O3, 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 1) A solution of the compound (0.500 g) obtained in Example 29, step 1, 4-benzyloxyphenylboronic acid (0.600 g) and potassium carbonate (0.243 g) in DME (10 mL) and water (1 mL) was degassed with argon gas, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.203 g) was added, and the reaction container was irradiated in a microwave reaction apparatus at 150C for 10 min. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The obtained solid was recrystallized from a mixed solution of ethyl acetate and hexane to give tert-butyl 8-[(benzyloxy)phenyl]-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.483 g, 64%) as a white powder. 1H-NMR(CDCl3): delta 1.32(9H,brs), 3.74(2H,brs), 4.24(2H,brs), 4.47(2H,brs), 5.17(2H,s), 7.09(2H,d,J=8.7Hz), 7.31-7.52(5H,m), 7.58(1H,m), 7.71(1H,m), 7.97(2H,d,J=8.7Hz) MS(ESI+):433(M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
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Electric Literature of 4424-80-0, A common heterocyclic compound, 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, molecular formula is C10H11NO, 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.

The starting material is prepared as follows: To a solution of 2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (2.5 g) in chloroform (30 ml), phosphorus pentachloride (3.2 g) was added in portions, while maintaining the temperature at 0¡ã-5¡ã. When the addition was complete, iodine (30 mg) was added followed by bromine (2.5 g), which was added dropwise over 5 minutes. The mixture was then refluxed for 4 hours. The chloroform solution was evaporated and the residue was partitioned between ice-water (30 ml) and dichloromethane (75 ml). The organic phase was dried over magnesium sulfate and evaporated under reduced pressure. The crude residue was purified by chromatography over silica gel, eluding with ether and hexane (7:3). Concentration of the appropriate fractions yielded 3-bromo-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one, m.p. 146¡ã-148¡ã.

The synthetic route of 4424-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4575503; (1986); A;; ; Patent; Ciba-Geigy Corporation; US4410520; (1983); A;,
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239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: amides-buliding-blocks

To a solution of tert-butyl N-[4-(hydroxymethyl)cyclohexyl]carbamate (S9, 0.92 g, 4.00mmol) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol) in CH2Cl2 (20 mL, 0.2 M) cooledto 0 C was added methanesulfonyl chloride (0.34 mL, 4.40 mmol) dropwise. After 5 min thereaction was warmed to 23 C and stirred for 2 h. A saturated solution of aqueous NaHCO (30mL) was added to quench the reaction. The organic phase was separated and the aqueous phasewas extracted with CH2Cl2 (2 ¡Á 10 mL). The combined organics were dried over MgSO4,filtered, and the filtrate was concentrated under reduced pressure. The crude material was driedunder hi-vac to afford crude [4-(tert-butoxycarbonylamino)cyclohexyl]methyl methanesulfonate(S10, 1.24 g, >99% yield) which was used without further purification.

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Allegretti, Paul A.; Horton, Timothy M.; Abdolazimi, Yassan; Moeller, Hannah P.; Yeh, Benjamin; Caffet, Matthew; Michel, Guillermina; Smith, Mark; Annes, Justin P.; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
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Related Products of 180079-94-1,Some common heterocyclic compound, 180079-94-1, name is tert-Butyl 3-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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.

Synthesis of TU71 N-Boc 3-(2′-amino)ethyl aniline (200 mg, 0.8 mmol), DCM (3 mL) and triethyl amine (0.15 mL) in a round bottom flask that had been flame dried in the presence of molecular sieves and cooled under vacuum was stirred at 4 C. After 10 min di 2-pyridyl thionocarbonate (200 mg, 0.8 mmol) was added. The reaction was stirred overnight at 4 C after which time the DCM layer was washed twice with water and once with brine. Chromatography on silica gel yielded the titled compound (0.1 g, 59 %) as a white solid. deltaEta (400 mHz, CDC13) 1.405 (9H, s), 2.753 (2H, t, J=6.8 Hz), 3.327 (2H, q, J=6.8 Hz), 4.611 (1H, br s), 7.036- 7.089 (3H, m), 7.228-7.266 (2H, m). 5C (100 mHz, CDC13) 28.65, 35.228, 41.301, 77.954, 133.806, 126.711, 129.006, 130.129, 133.727, 142.175, 155.936. m/z 279 (MH+). HREIMS found 279.1170 C14H19N202S, requires 279.1167.

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

Reference:
Patent; BRANDEIS UNIVERSITY; HEDSTROM, Lizbeth, K.; LONG, Marcus, J.; LAWSON, Ann, Parrinello; (70 pag.)WO2016/14522; (2016); A1;,
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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. 202207-79-2, name is 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H19ClN2O2

Reference Example 1 Synthesis of benzyl 4-((2-((tert-butoxycarbonyl)amino)ethyl)(methyl)amino)piperidine-1-carboxylate (0330) (0331) tert-Butyl (2-(methylamino)ethyl)carbamate hydrochloride (0.564 g, 2.68 mmol) and sodium triacetoxyborohydride (0.681 g, 3.22 mmol) were added to a solution of benzyl 4-oxopiperidine-1-carboxylate (0.500 g, 2.14 mmol) in dichloromethane (3.0 mL) at 0 C., and the resulting mixture was stirred at room temperature for 16 hours. The reaction liquid was cooled to 0 C. A saturated aqueous solution of sodium hydrogencarbonate was added to the reaction liquid, and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, hexane/ethyl acetate) to obtain benzyl 4-((2-((tert-butoxycarbonyl)amino)ethyl)(methyl)amino)piperidine-1-carboxylate (0.590 g, 1.51 mmol, 70%) as a white solid. (0332) 1H-NMR (400 MHz, CDCl3) delta: 1.38-1.46 (11H, m), 1.67-1.76 (2H, m), 2.22 (3H, s), 2.47-2.55 (3H, m), 2.64-2.82 (2H, m), 3.12-3.21 (2H, m), 4.16-4.32 (2H, m), 4.90-5.00 (1H, m), 5.12 (2H, s), 7.30-7.37 (5H, m). (0333) ESI-MS: m/z=392 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 202207-79-2.

Reference:
Patent; Toray Industries, Inc.; MORITA, Yasuhiro; IZUMIMOTO, Naoki; ISEKI, Katsuhiko; IWANO, Shunsuke; UDAGAWA, Shuji; MIYOSHI, Tomoya; OSADA, Yuji; KOREEDA, Tetsuro; MURAKAMI, Masanori; SHIRAKI, Motohiro; TAKAHASHI, Kei; OSHIDA, Keiyu; (91 pag.)US2016/194302; (2016); A1;,
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