Month: February 2021

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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-(2-Aminoethyl)benzenesulfonamide

To a solution of 1- (3-isocyanatopropyl) -4-methoxybenzene (0.78 mmol) in THFWas added 4- (2-aminoethyl) benzenesulfonamide (0.86 mmol) at room temperature to a solution (20 ml)Was slowly added over 10-15 minutes. The reaction mixture was stirred at 40-45 [deg.] C for 24 hours. The next day TLC confirmed the termination of the reaction. The solvent was distilled off and ammonium chloride (100 & lt; RTI ID = 0.0 & gt;Ml), 1N HCl solution (50 ml) and ethyl acetate (100 ml). The organic layer was washed with brine and then dried with sodium sulfate. The solvent was distilled off and the residue was adsorbed onto silica gel using methylene chloride. The title compound was then purified by column chromatography using ethyl acetate and hexane.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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Related Products of 72080-83-2, A common heterocyclic compound, 72080-83-2, name is Benzyl (2-aminoethyl)carbamate, molecular formula is C10H14N2O2, 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.

1-((Dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V) (HATU, 1.87 g, 4.92 mmol) and triethylamine (3.43 mL, 24.6 mmol) were subsequently added to a solution of (S)-22-(tert-butoxycarbonyl)-10,19,24-trioxo-39-sulfo-3,6,12,15-tetraoxa-9,18,23-triazanonatriacontanoic acid (4.5 mmol) in dry dichloromethane (40 mL). Triethylamine (1.82 mL, 13.1 mmol) was added to a suspension of (2-amino-ethyl)-carbamic acid benzyl ester hydrochloride (5, 1.93 g, 8.37 mmol) in dry dichloromethane (20 mL) and the resulting mixture was added to the above solution. The mixture was stirred overnight at room temperature. After 16 hours, another portion of 1-((dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V) (HATU, 0.38 g, 1 mmol), triethylamine (2.00 mL, 14.3 mmol) and (2-amino-ethyl)-carbamic acid benzyl ester hydrochloride (5, 0.40 g, 1.70 mmol) were added and the mixture was stirred for another 2 hours. The solution was washed with 1 M aqueous hydrochloric acid (2¡Á100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and evaporated to dryness. Crude (S)-29-(tert-butoxycarbonyl)-3,8,17,26,31-pentaoxo-1-phenyl-2,10,13,19,22-pentaoxa-4,7,16,25,30-pentaazahexatetracontane-46-sulfonic acid (6) was used for the next step without further purification. (0579) Yield: quantitative (based on ELSD). (0580) LC-MS purity: 83% (ELSD). (0581) LC-MS Rt (Kinetex C18, 4.6 mm¡Á50 mm, acetonitrile/water 20:80 to 100:0+0.1% FA): 3.35 min. (0582) LC-MS m/z: 989.1 (M+H)+.

The synthetic route of 72080-83-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; Gao, Xiang; Zhang, Xujia; Guan, Hongtao; Thoegersen, Henning; Sass-Oerum, Kristian; Iversen, Lars Fogh; Noergaard, Per; Joergensen, Sebastian Beck; Hansen, Kristian Tage; Wang, Yi; Frieboes, Kilian Waldemar Conde; Wieczorek, Birgit; (259 pag.)US2018/339057; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6919-61-5, name is N-Methoxy-N-methylbenzamide, belongs to amides-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 6919-61-5, name: N-Methoxy-N-methylbenzamide

N-Methoxy-N-methyl benzamide 20 (0.1 g, 0.60 mmol) was dissolved in anhydrous diethyl ether (2.01 ml). The solution was cooled to 0 C. To this, vinyl magnesium bromide solution (0.91 ml, 1.0 M in THF) was added dropwise over 30 min at 0 C. After the completion of addition, the reaction mixture was stirred for a further 60 min at 0 C and for 30 min at room temperature. It was then quenched with 1M HCl at 0 C. The reaction mixture was diluted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4,concentrated in vacuo, purified on silica gel (3:1 hexanes/EtOAc) to afford 0.04 g of 7 (55%) as a colorless oil. 1H NMR (400 MHz, CDCl3) ae 7.95 (d, J = 8.3 Hz, 2H), 7.60-7.55 (m, J = 7.4 Hz,1H), 7.49 (t, J = 8.0 Hz, 2H), 7.15 (dd, J = 10.5 Hz, 6.6 Hz, 1H), 6.40 (d, J = 17.1 Hz, 1H), 5.90(d, J = 10.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) ae 191.2, 137.5, 133.1, 132.6, 130.2, 128.8,128.7. HRMS C9H9O [M+H]+ Expected: 133.0648, Found: 133.0646.

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, N-Methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Korwar, Sudha; Nguyen, Thuy; Ellis, Keith C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 271 – 274;,
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Reference of 207405-68-3, The chemical industry reduces the impact on the environment during synthesis 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, I believe this compound will play a more active role in future production and life.

General procedure: To the solution of compound 13 (0.11 g, 0.25 mmol) and bicyclicamine (0.38 mmol) in THF (3 mL) was added DIPEA (0.38 mmol). Afterstirred at R.T. for 1 h, the reaction mixture was diluted with EtOAc,washed with brine, dried over MgSO4, and evaporated. The residue waspurified by column chromatography to give the product.4.1.6. tert-butyl (endo)-3-((2,6-dichloro-8-((2-fluoro-4-(methylsulfonyl)phenyl)amino)pyrimido[5,4-d]pyrimidin-4-yl)amino)-8-azabicyclo[3.2.1]octane-8-carboxylate (14a)Yellow solid, 32% yield. 1H NMR (300 MHz, CDCl3) delta (ppm): 9.12(d, J=3.2 Hz, 1H), 8.95 (t, J=8.1 Hz, 1H), 7.80 (m, 2H), 7.45 (d,J=7.7 Hz, 1H), 4.50-4.20 (m, 3H), 3.10 (s, 3H), 2.50-2.10 (m, 4H),2.00-1.80 (m, 4H), 1.50 (s, 9H). HRMS-ESI (m/z) calcd forC25H28Cl2FN7O4S [M+Na]+: 634.1182, found 634.1234

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, tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fang, Yuanying; Xu, Jun; Li, Zhifeng; Yang, Zunhua; Xiong, Lijuan; Jin, Yi; Wang, Qi; Xie, Saisai; Zhu, Wufu; Chang, Sheng; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4080 – 4087;,
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156731-40-7, name is 1-(Boc-amino)-3-butene, 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. COA of Formula: C9H17NO2

Sodium hydride (583 mg of 60% dispersion in mineral oil, 14.6 mmol) was washed twice with 16 mL portions of hexane and suspended in 16 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl but-3-enylcarbamate (830 mg, 4.85 mmol) was added dropwise. Reaction mixture was warmed up to room temperature and stirred under argon for 30 min. Reaction mixture was cooled to 0C and freshly distilled ethyl iodide (0.78 mL, 9.7 mmol) was added dropwise. Reaction mixture was allowed to warm up to room temperature overnight, and it was then cooled to 0C and quenched with saturated ammonium chloride solution. The layers were separated and aqueous layer was extracted with Et2O. Organics were combined and washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Crude reaction mixture was purified by flash column chromatography (hexanes:EtOAc 4:1) to give 900 mg (93%) of the title compound as a colorless oil. IR (neat) 3078, 2976, 2932, 2871, 1685 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.04-1.09 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 2.20-2.27 (m, 2H), 3.19 (br m, 4H), 4.95-5.06 (m, 2H), 5.67-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 11.58, 26.45, 31.25, 39.90, 44.32, 77.01, 114.33, 133.62, 153.36; m/z (relative intensity) 199(1), 158(5), 102(8), 57(100), 41(70), 29(52). Anal.Calcd. for C11H21NO2: C, 66.29; H, 10.62; O, 16.06. Found: C, 66.07; H, 10.66; O, 15.95.

The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
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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.

Cbz-glycine (2.92 g, 13.89 mmol) and 120 mL of acetonitrile were added to a 250 mL reaction flask, stirred and dissolved, and CDI (2.57 g, 15.85 mmol) was slowly added, and reacted at 45 C for 1.5 hours. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), Intermediate VII (2 g, 13.23 mmol) was added and reacted at 45 C for 4 hours. TLC (dichloromethane: methanol = 10:1) monitoringAfter the raw materials are reacted, a large amount of white solid is produced, suction filtered, and dried. It was added to a 100 mL reaction flask, 50 mL of glacial acetic acid was added, and the reaction was refluxed at 120 C. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), the glacial acetic acid was concentrated under reduced pressure and dissolved in 100 mL of water.Extracted with ethyl acetate (100 mL ¡Á 2), and the organic layer was combined.Wash with saturated sodium chloride (150 mL) and dry over anhydrous sodium sulfate. Filtered off with suction, the filtrate was concentrated to give the crude product (VIII) 4.18g, yield 97.4%.

Statistics shows that 2,3-Diaminobenzamide is playing an increasingly important role. we look forward to future research findings about 711007-44-2.

Reference:
Patent; China Pharmaceutical University; Xu Yungen; Zhu Qihua; Ge Yiran; Li Hui; Zhang Guangxia; Wang Junwei; (21 pag.)CN109748923; (2019); A;,
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Related Products of 1520-70-3,Some common heterocyclic compound, 1520-70-3, name is Ethanesulfonamide, molecular formula is C2H7NO2S, 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 stirred solution of free acid (50 mg, 0.11 mmol) from Example 226 in 1 ML of methylene chloride was added ethyl sulfonamide (18 mg, 0.17 mmol), EDAC (25 mg, 0.13 mmol), and DAMP (2.7 mg, 0.022 mmol) sequentially.The mixture was stirred at ambient temperature for 16 h.The solvent was then removed on a rotavap under reduced pressure and the residue was purified on an Alltech sep-pak, eluding with 1percent MeOH in EtOAc to give 30 mg (50percent yield) of the title compound as a light yellow solid. 1H NMR (CDCl3, 300 MHz) delta 1.18 (d, J=6.3 Hz, 6H), 1.34 (t, J=7.5 Hz, 3H), 1.61-1.74 (m, 2H), 1.84-2.04 (m, 1H), 2.13-2.35 (m, 1H), 2.60-2.75 (m, 2H), 3.44 (p, J=7.5 Hz, 2H), 3.53-3.66 (m, 1H), 3.66-3.85 (m, 2H), 4.00-4.18 (m, 1H), 6.71 (d, J=8.7 Hz, 1H), 6.88 (d, J=15.6 Hz, 1H), 7.31 (dd, J=2.4, 8.4 Hz, 1H), 7.41 (d, J=1.8, 8.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.67 (d, J=15.6 Hz, 1H), 8.43 (s, 1H). MS (ESI+) (M+H)+ at m/z 546.

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

Reference:
Patent; Abbott Laboratories; US2004/116518; (2004); 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H18N2O2

Reference Example 61Synthesis of tert-butyl methyl-[2-(2-nitrobenzenesulfonylamino) ethyl]carbamate2-Nitrobenzenesulfonyl chloride (4.9 g, 22 mmol) was added to a dichloromethane solution (100 ml) of tert-butyl (2-aminoethyl)methyl carbamate (3.5 g, 20mmol) and triethylamine (3.3ml, 24 mmol) at 0C, and stirred at room temperature overnight. Waterwas added to the reaction mixture, and extraction with dichloromethanewas performed. The organic layer was dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The residue waspurified by silica gel column chromatography (n-hexane:ethylacetate=3:2-?2:3) . The purified product was concentrated underreduced pressure to thereby obtain 5.06 g (yield: 70%) of tert-butylmethyl-[2-(2-nitrobenzenesulfonylamino)ethyl]carbamate as a yellowoil.1H-NMR (CDC13) 5ppm:1.45 (9H, s), 2.84 (3H, s), 3.26 – 3.41 (4H, m), 7.68-7.79 (2H, m),7.79-7.90 (1H, m), 8.09-8.19 (1H, m) .

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2009/104819; (2009); 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. 7700-07-4, name is N,N-Dimethylethenesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C4H9NO2S

To a solution of Example 1.18.18 (69.8 mg) in N,N-dimethylformamide (6 mL) was added N,N-dimethylethenesulfonamide (118 mg), N,N-diisopropylethylamine (0.2 mL) and H20 (0.2 mL). The mixture was stirred at room temperature 4 days. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water and brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was dissolved in dichloromethane and trifluoroacetic acid (10 mL, 1 :1), and the resulting solution was stirred overnight. The solvents were removed under reduced pressure. The residue was diluted with N,N-dimethylformamide (2 mL), filtered and purified by reverse-phase HPLC on a Gilson system (CI 8 column), eluting with 20-80% acetonitrile in water containing 0.1% trifluoroacetic acid, to give the title compound. NMR (400 MHz, dimethyl sulfoxide-^) delta ppm 12.82 (s, 1H), 8.53 (s, 2H), 8.00 (dd, 1H), 7.76 (d, 1H), 7.59 (dd, 1H), 7.53 – 7.37 (m, 4H), 7.37 – 7.28 (m, 2H), 7.26 (s, 1H), 6.92 (d, 1H), 4.92 (s, 2H), 3.80 (s, 2H), 3.54 (t, 2H), 3.44 – 3.34 (m, 2H), 3.30 (s, 2H), 3.11 (s, 2H), 2.98 (t, 2H), 2.77 (s, 6H), 2.07 (s, 3H), 1.39 (s, 2H), 1.27 (q, 4H), 1.11 (s, 4H), 1.06 – 0.93 (m, 2H), 0.83 (s, 7H). MS (ESI) m/e 881.2 (M+H)+.

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; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
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337463-88-4, name is 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, 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. HPLC of Formula: C7H5BrN2O2

To a stirred solution of lla (32 g, 0.139 mol) and 6-bromo-2H-pyrido[3,2-b][l,4]oxazin- 3(4H)-one (WO2017199265, 31.7 g, 0.139 mol) in dry l,4-dioxane (50 mL), were added t-butyl-X-Phos mesyl chloride complex( 5.5 g, 0.0069 mol) and sodium tert-butoxide (19.94 g, 0.207 mol) and was degassed for 20 mins. Then, it was heated in sealed tube at 100 C for 16 h. After completion of the reaction, reaction mixture was concentrated under reduced pressure. It was purified by column chromatography on silica gel (230-400 mesh, 25-30% ethyl acetate in pet ether) to afford lib (45.6 g, 86%). LC_MS Calculated for C17H25N3O5S1, 379.49, Observed 380.0. lH NMR (400 MHz, DMSO-d6). d 7.60 (d, J = 8.68 Hz, 1H), 7.43 (d, J = 8.68 Hz, 1H), 4.77-4.73 (m, 1H), 4.67 (s, 2H), 4.15-4.10 (m, 1H), 3.93-3.89 (m, 3H), 0.79 (s, 9H), 0.04 (s, 6H).

The synthetic route of 337463-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; RAMACHANDRAN, Vasanthi; (116 pag.)WO2019/186590; (2019); A1;,
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