Month: February 2021

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 67442-07-3, The chemical industry reduces the impact on the environment during synthesis 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, I believe this compound will play a more active role in future production and life.

To a solution of trimethylsulfonium iodide (41.51 g, 203.9 mmol) in THF (335.3 mL)at -30 ¡ãC was added lithium bis(trimethylsilyl)amide (1M in heptane, 203.9 mL, 203.9mmol) portionwise over 45 mills. After stirring for 30 mins, 3,3,3-trifluoro-1,2- epoxypropane (14 g, 124.9 mmol) was added at -20 ¡ãC over 15 mill, and the mixture was allowed to warm to RT and stirred for 3 h and 10 mm. The slurry was then added portionwise to an ice-cold solution of 2-chloro-N-methoxy-N-methylacetamide (28.05g, 203.9 mmol) in NMP (75.7 mL). The resulting mixture was allowed to warm to RT and stirred for 1 day before dilution with EtOAc. The organic layer was washed with NaHCO3 (sat. aq. sol.) and the washings extracted with EtOAc. The organic layers were combined, dried (MgSO4) and evaporated. The residue was purified by column chromatography (silica gel; n-heptane/EtOAc 100/0 to 70/30) to yield 1-1 (13.8 g,49percent).

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-Chloro-N-methoxy-N-methylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; (134 pag.)WO2018/83247; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 2895-21-8, A common heterocyclic compound, 2895-21-8, name is N-Isopropyl-2-chloroacetamide, molecular formula is C5H10ClNO, 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.

Compound 1d (18 mg, 0.08 mmol) was dissolved in 1.5 mL of DMF,Potassium carbonate (22.2 mg, 0.16 mmol) was added,80 reaction 30min,Compound 3a (13.1 mg, 0.10 mmol) was added,80 C overnight.After the reaction is over,Cool to room temperature.Add appropriate amount of water,Ethyl acetate was extracted three times,The organic phases were combined and washed with saturated brine,Dried over anhydrous magnesium sulfate,The crude product was distilled under reduced pressure.Separation and purification by column chromatography,25.0 mg of a white solid.Yield: 96.2%

The synthetic route of 2895-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; Chen, Jianzhong; Xie, Xin; Qian, Haiyan; Chen, Lili; Wang, Zhilong; (42 pag.)CN106167497; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 40724-47-8, 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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

[0330] Isopropyl 2-(4-bromo-3 -(3 -isopropoxyphenyl)- 1H-pyrazol- 1 -yl)thiazole-4- carboxylate (520 mg, 1.15 mmol) was dissolved in anhydrous THF ( 5 mL) and potassium acetate (340 mg, 3.46 mmol), PdC12(dppf) (0.9 mg, 0.0011 mmol) and bis(pinacolato)diborane (408 mg, 1.61 mmol) were added. The vial was purged with argon for 5 mm. The reaction was heated at 100 ¡ãC for 2h. The reaction mixture was diluted with ethyl acetate and filtered through a plug of celite. The solvent was removed by rotary evaporator and purified by flash chromatography (Combi-flash Rf, hexane/ethyl acetate, 0- 40percent gradient) to give a mixture of isopropyl 2-(3-(3-isopropoxyphenyl)-4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazol- 1 -yl)thiazole-4-carboxylate and isopropyl 2-(3 -(3 -isopropoxyphenyl)- 1 H-pyrazol- 1 -yl)thiazole-4-carboxylate.

The chemical industry reduces the impact on the environment during synthesis 4-Bromomethylbenzenesulfonamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16695-22-0, 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. 16695-22-0, name is (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate), This compound has unique chemical properties. The synthetic route is as follows.

9 was obtained from myricetin (509 mg, 1.6 mmol), K2CO3 (276 mg, 2.0 mmol), N,O,O’-Tri(toluene-4-sulfonyl)diethanolamine (454 mg, 0.8 mmol) and DMF (30 mL), according to the general procedure, as a light yellow amorphous powder (402 mg, yield: 45%); UV (MeOH) lambdamax(log epsilon) 364 (2.56) nm; IR (K Br)numax: 3397, 2923, 1656, 1160, 1048 cm-1. 1H NMR (DMSO-d6, 400 MHz): delta 12.39 (1H, br s, 5-OH), 7.63 (2H, d, J = 8.0 Hz, H-6″, 10″), 7.47 (1H, s, H-2′), 7.38 (2H, d, J = 8.0 Hz, H-7″, 9″), 7.31 (1H, s, H-6′), 6.43 (1H, s, H-8), 6.20 (1H, s, H-6), 4.41 (2H, br s, H-1″), 4.23 (2H, br s, H-2″), 3.44 (4H, br s, H-3″, 4″), 2.36 (3H, s, H-11″); 13C NMR (DMSO-d6, 100 MHz): delta 176.1 (C-4), 164.5 (C-7), 160.7 (C-5), 156.2 (C-9), 152.5 (C-3′), 150.6 (C-5′), 145.2 (C-2), 143.3 (C-8″), 140.9 (C-5″), 136.9 (C-4′), 135.1 (C-3), 129.9 (C-7″, 9″), 126.9 (C-6″, 10″), 126.1 (C-1′), 111.9 (C-6′), 110.2 (C-2′), 103.0 (C-10), 98.4 (C-6), 93.5 (C-8), 73.2 (C-1″), 72.7 (C-4″), 52.2 (C-3″), 51.9 (C-2″), 20.9 (C-11″); HRESIMS m/z 542.1113 [M-H2O+H]+ (calcd for [C26H24NO10S]+, 542.1115).

The chemical industry reduces the impact on the environment during synthesis (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate). I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Jia; Wu, Yuechan; Zou, Jianwei; Gao, Kun; Bioorganic and Medicinal Chemistry; vol. 24; 7; (2016); p. 1488 – 1494;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 22726-00-7, name is 3-Bromobenzamide, molecular formula is C7H6BrNO, 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. HPLC of Formula: C7H6BrNO

A mixture of 3-bromobenzamide (3 g, 15.1 mmol), [3-(hydroxymethyl)- phenyl]boronic acid (3 g, 19.6 mmol), PdCl2(PPh3)2 (0.46 g, 0.66 mmol), and potassium carbonate (3.6 g, 26.2 mmol) in Toluene/MeOH (10:1, 40 mL) was stirred at 80 C for 18 h. The resulting black mixture was cooled to room temperature, filtered through celite, and poured into a EtO Ac/brine mixture. The two layers were separated and the aqueous was extracted with EtOAc (3x). The organics were combined, dried over sodium sulfate, filtered, and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with a mixture of EtOAc/Hexane to give 3′-(hydroxymethyl)biphenyl-3-carboxamide 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 22726-00-7, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2006/14918; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 711007-44-2, These common heterocyclic compound, 711007-44-2, name is 2,3-Diaminobenzamide, 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.

Step-4: To a solution of 2-((benzyloxy)carbonyl)-3-methyl-l,2,3,4- tetrahydroisoquinoline-3-carboxylic acid (620 mg, 1.91 mmol) in anhydrous DMF (5 ml) was added EDCHCl (1.098 mg, 5.73 mmol), HOAt (390 mg, 2.87 mmol) and triethylamine (0.4 ml, 2.87 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3- diaminobenzamide (346 mg, 2.29 mmol) was added and heated to 550C for 3 days. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum and purified by preparative TLC using ethyl acetate as eluent to afford benzyl 3-((2-amino-3-carbamoylphenyl)carbamoyl)-3-methyl-3,4-dihydroisoquinoline- 2(lH)-carboxylate. MS (ES+): m/z 481.2 [M+ Na]+

The synthetic route of 711007-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGION BIOMEDICA CORP.; PANICKER, Bijoy; LIM, Dong, Sung; SMITH, David, E.; WO2011/2520; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics