Amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 6325-93-5, name is 4-Nitrobenzenesulfonamide, 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 6325-93-5, COA of Formula: C6H6N2O4S

Step 1 – Tert-butyl N-(4-nitrophenyl)sulfonylcarbamate (0596) [00375] To a solution of 4-nitrobenzenesulfonamide (5.00 g, 24.7 mmol) in anhydrous dichloromethane (40 mL) was added triethylamine (5.00 g, 49.4 mmol) and catalytic amount of N,N-dimethylpyridin-4-amine. The mixture was cooled to 0 C and di-tert-butyl dicarbonate (5.67 g, 25.9 mmol) was added over 10 min. Then the mixture was warmed to 18 C and stirred for 50 min. On completion, the reaction mixture was quenched with ice water (40 mL). Afterwards, the organic phase was separated, washed with brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 3:1 to 1:1) to give the title compound.1H NMR (400MHz, CDCl3) delta = 8.44 – 8.40 (m, 2H), 8.28 – 8.24 (m, 2H), 1.43 (s, 9H).

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Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
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A common compound: 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 16982-21-1

N,6-dimethylnicotinohydrazide (23a, 0.1 g, 0.61 mmol) and ethyl 2-amino-2-thioxoacetate (0.089 g, 0.67 mmol) in toluene (0.5 mL) and acetic acid (0.05 mL) were stirred at 90 C for 10 hours. The reaction mixture was purified by preparative HPLC using a Gemini NX reverse-phase column (C-18, 5 microns silica, 30 mm diameter, 150 mm length, flow rate of 60 ml / minute) using an isocratic mixture of 17% acetonitrile in water (containing ammonium carbonate (2 g / L). The fractions containing the desired compound were evaporated to dryness to afford ethyl 1-methyl-5-(6-methylpyridin-3-yl)-1H-1,2,4-triazole-3-carboxylate (34a, 0.083 g, 55%) as a yellow crystalline solid: 1H NMR (500 MHz, DMSO-d6) delta 8.87 (d, J = 1.9 Hz, 1H), 8.13 (dd, J = 1.9, 8.1 Hz, 1H), 7.49 (d, J = 8.1 Hz, 1H), 4.36 (q, J = 7.1 Hz, 2H), 4.06 (s, 3H), 2.58 (s, 3H), 1.33 (t, J = 7.1 Hz, 3H); 13C NMR (126 MHz, DMSO-d6) delta (ppm) 161.34, 158.91, 156.03, 151.34, 150.14, 136.39, 124.11, 118.93, 63.45, 37.12, 24.34, 14.38; HRMS, ESI+ m/z, (M+H)+ calculated for C12H14N4O2 257.10330; found, 247.11879 (tR = 1.20 min., purity = 100%).

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, 16982-21-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Degorce, Sebastien; Delouvrie, Benedicte; Davey, Paul R.J.; Didelot, Myriam; Germain, Herve; Harris, Craig S.; Brempt, Christine Lambert-Van Der; Lebraud, Honorine; Ouvry, Gilles; Tetrahedron Letters; vol. 53; 45; (2012); p. 6078 – 6082;,
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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 35303-76-5 as follows. HPLC of Formula: C8H12N2O2S

To solid reagents 4-(2-aminoethyl)benzenesulfonamide (2.00 g, 9.99 mmol) and dihydrofuran-2,5-dione (0.999 g, 9.99 mmol) was added THF (30 mL). The reaction mixture was stirred at 60 C for 7 hrs. Solvent was evaporated under reduced pressure to give 4-oxo-4-((4- sulfamoylphenethyl)amino)butanoic acid (3.00 g, 9.99 mmol, 100 % yield) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 12.09 (s, 1H), 7.96 (t, J = 5.6 Hz, 1H), 7.72 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 8.1 Hz, 2H), 7.29 (s, 2H), 3.26 (q, J = 6.8 Hz, 2H), 2.76 (t, J = 7.2 Hz, 2H), 2.40 (t, J = 6.9 Hz, 2H), 2.27 (t, J = 6.9 Hz, 2H); MS (ESI), 301.1 (M+H)+.

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; WAVE LIFE SCIENCES LTD.; ZHANG, Jason Jingxin; SHIVALILA, Chikdu Shakti; VARGEESE, Chandra; IWAMOTO, Naoki; (469 pag.)WO2019/75357; (2019); A1;,
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Related Products of 70-55-3, 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. 70-55-3, name is 4-Methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, a mixture of sulfonamide (1 mmol), acylating agent(2 mmol) and Cs5HP2W18O62 catalyst (5 mmol %) in water (2 mL), was stirred at roomtemperature to obtain compounds (2a-j), (3a-m), (5a-f), and under reflux for (3n-r).The reaction was monitored by TLC. After completion of the reaction, the catalyst wasremoved by filtration. The filtrate was washed by water (10 mL) and extracted withEtOAc (315 mL). The combined organic layers were dried over anhydrous Na2SO4,then the solvent was evaporated in vacuum and the crude compound was purified byflash chromatography (Merck silica gel 60 H, CH2Cl2/MeOH, 9:1) to afford the corresponding products.

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-Methylbenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Benali, Nesma; Bougheloum, Chafika; Alioua, Sabrina; Belghiche, Robila; Messalhi, Abdelrani; Synthetic Communications; vol. 48; 24; (2018); p. 3099 – 3112;,
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Electric Literature of 85006-25-3,Some common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, 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.

Tert-butyl (tert-butoxycarbonyl)oxycarbamate (70 mg) and 1- (bromomethyl) -2-fluorobenzene (56.7 mg) were dissolved in CH 2Cl 2(7 ml) . The mixture was added 1M NaOH (0.33 ml) and tetrabutylammonium bromide(4.83 mg) , and stirred at room temperature for overnight. The resulting mixture was washed with water and dried with Na 2SO 4, concentrated in vacuo and purification by silica gel chromatography to give tert-butyl ( (tert-butoxycarbonyl) oxy) (2-fluorobenzyl) carbamate (82 mg, 80%) . 1HNMR (400 MHz, CDCl 3): delta 7.31-7.37 (m, 4H) , 4.52(s, 2H) , 1.46 (s, 9H) , 1.44 (s, 9H) .

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 (tert-butoxycarbonyl)oxycarbamate, its application will become more common.

Reference:
Patent; SU, Yaning; SIRONAX LTD; ZHANG, Zhiyuan; YANG, Yi; WANG, Guozheng; LIU, Wendong; MA, Yongfen; REN, Yan; (74 pag.)WO2020/103859; (2020); A1;,
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Related Products of 207405-68-3, 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. 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound ii-35a (5.00 g, 22.19 mmol) in methanol (100 mL) and water (10 mL) were added ammonium formate (13.99 g, 222 mmol) and 10%-palladium/carbon (2.362 g) in turn. The resultant was stirred at room temperature for 2 days. Celite was used to filtrate the reaction liquid, and then the filtrate was diluted with chloroform, washed with an aqueous sodium hydroxide solution and a saturated salt solution, and dried over magnesium sulfate. Magnesium sulfate was filtrated off, and then the liquid was concentrated under reduced pressure to yield compound ii-35b (5.60 g). Compound ii-35b yielded was used as it was, without being purified, in the next reaction.The total amount of compound ii-35b yielded was dissolved in methanol (50 mL) and acetic acid (5 mL). Thereto were then added a 36% aqueous formalin solution (8.49 mL, 111 mmol) and hydrogenated sodium triacetoxyborate (9.41 g, 44.4 mmol) in turn. The resultant was stirred at room temperature for 1 hour. To the reaction liquid was added an 8 N aqueous sodium hydroxide solution to set the pH thereof to 10. Thereafter, this liquid system was subjected to extraction with chloroform. To the organic phase was added a 0.5 N aqueous hydrochloric acid solution, and then the liquid-system was separated to two phases. Thereafter, the water phase was made into basicity, and then subjected to extraction with chloroform. The organic phase was washed with a saturated salt solution, and dried over magnesium sulfate. Magnesium sulfate was filtrated off, and then the organic phase was concentrated under reduced pressure to yield compound ii-35c (2.43 g, 43%).1H-NMR (CDCl3) delta: 4.16 (2H, d, J = 29.04 Hz), 2.22 (6H, s), 2.12-1.59 (9H, m), 1.46 (9H, s).

The synthetic route of tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; HISAKAWA, Shinya; HASEGAWA, Yasushi; AOKI, Toshiaki; KUSANO, Hiroki; SANO, Masayuki; SATO, Jun; YAMAWAKI, Kenji; EP2557082; (2013); A1;,
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Synthetic Route of 116861-31-5, 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 116861-31-5 as follows.

Synthesis of compound 22: the aforementioned compound 20 (0.120 g, 0.00049 mol, 1 eq) was solubilised in DMF (3 ml). To the solution was added the aforementioned compound 21 (0.104 g, 0.00054 mol, 1.1 eq) solubilised in DMF (2 ml). The reaction mixture was stirred under reflux for 6 hours. The structure of the product was evaluated by TLC CH2Cl2 9/MeOH 1/NH4OHaq 33% 0.03. The solvent was evaporated, and the oily residue was purified by flash chromatography using a mixture of CH2Cl2 9/MeOH 1/NH4OHaq 33% 0.03 as the eluent phase. 0.084 mg of a yellow oil were obtained. Yield 42.71%. 1H NMR (400 MHz, CDCl3) delta 0.87 (d, 6H, J=6.8 Hz), 1.43 (s, 18H), 1.57-1.61 (m, 7H), 1.98-2.01 (m, 2H), 2.31-2.35 (m, 2H), 2.38-2.42 (m, 2H), 3.10-3.12 (m, 2H), 3.16-3.18 (m, 2H), 4.72 (brs, 1H, exch D2O), 5.69 (brs, 1H, D2O exch.).

According to the analysis of related databases, 116861-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Giuliani, Giammaria; Paus, Ralf; Benedusi, Anna; Marzani, Barbara; Baroni, Sergio; US2015/202132; (2015); A1;,
Amide – Wikipedia,
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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 683-57-8 as follows. Product Details of 683-57-8

Example 1: 2-[1-(2-Morpholin-4-yl-ethoxy)-naphthalen-2-ylamino]-acetamide, hydrochloride; [Show Image] 2-Bromoacetamide (1.05 equiv), potassium carbonate (1.5 equiv) and sodium iodide (0.1 equiv) were added at r.t. to a solution of 1-(2-Morpholin-4-yl-ethoxy)-naphthalen-2-ylamine (50 mg, 0.18 mmol) in acetonitrile (3 mL). The resulting mixture was allowed to heat to 80C for 18 hours. water (10 mL) and DCM (10 mL) were added to the mixture. The organic layer was washed with water (1x) and brine (2x). After drying over MgSO4, the solvent was evaporated to afford the crude compound. This latter was purified by flash chromatography (100% EtOAc to 10% MeOH/EtOAC) to afford brown oil in 63 % yield. A 2.0 M solution of HCl in ether (10 equiv) was added to a solution of this latter in 0.5 mL of methanol to afford the HCl salt as an brown hygroscopic solid. 1H NMR (400 MHz, CD3OD) : 3.38 (s, 2H, CH2-N), 3.86 (t, J 4.9 Hz, 4H, CH2-N), 4.0-4.1 (m, 4H, CH2-O), 4.14 (s, 2H, NH-CH2-CO), 4.57 (t, J 4.8 Hz, 2H, CH2-CO), 7.31 (d, J 9.3 Hz, 1H, Ar), 7.45 (m, 1H, Ar), 7.60 (m, 1H, Ar), 7.60 (m, 1H, Ar), 7.77 (d, J 8.8 Hz, 1H, Ar), 7.90 (d, J 7.8 Hz, 1H, Ar), 8.02 (d, J 9.3 Hz, 1H, Ar). M/Z (M+H)+ = 330.

According to the analysis of related databases, 683-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Faust Pharmaceuticals; EP1777219; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 98-18-0, A common heterocyclic compound, 98-18-0, name is 3-Aminobenzenesulfonamide, molecular formula is C6H8N2O2S, 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.

First the starting material, 3-isothiocyanato-benzenesulfonamide, which has the structural formula was prepared as follows. To a solution of 3-AMINO- benzenesulfonamide (Maybridge Chemical Co. , 1.00 g, 5.81 MMOL) in acetone (15 mL) at 0°C was added sequentially thiophosgene (0.503 mL, 6.39 MMOL) and fresh 25percent aq. NA2CO3 (5. 8 mL). The mixture was allowed to warm to ambient temperature. After 20 minutes, the acetone was removed under reduced pressure. The resultant suspension was adjusted to pH=7 with 10percent aq. HCI and filtered to isolate a light tan solid, 1.24 G (quantitative yield), that matched previous (mp 146-149°C ; French patent application FR 1528249; Chem. Abs. , 71, 30206 (1969) ) and was used without further purification. 1H NMR (DMSO-d6) : 87. 83-7.75 (1H, m), 7.69-7. 62 (1H, m), 7.52 (1H, s). The title compound was prepared in a manner similar to that for 4- [4-AMINO-5- (2- hydroxy-2-methyl-propionyl)-thiazol-2-ylamino]-benzenesulfonamide (Example M (1)). 3- ISOTHIOCYANATO-BENZENESULFONAMIDE (212 mg, 0.989 MMOL) furnished a yellow solid, 432 mg, that precipitated from IPROH/HEX to give 17. 1 mg of orange-brown solid. Furthermore, the mother liquor was purified via column, chromatography with a 5-10percent MeOH/CHCI3 stepwise gradient eluant to provide 120 mg of yellow solid that decomposed above 240 C. The total yield was 291 mg (73percent). 1H NMR (CD30D) : 8 8.36 (1H, dd, J = 1.8, 1.8 Hz), 7.78 (1H, ddd, J = 1.0, 2.2, 8.1 Hz), 7.62 (1H, ddd, J = 1. 1,1. 6,7. 8 HZ), 7.50 (1H, t, J = 8. 1 Hz), 7.05 (2H, t, J = 7. 5 HZ). FTIR (KBr): 3309,3076, 1620, 1546,1527, 1465,1429, 1156 cm-1. HRFABMS: Calcd for CR6H 3F2N403S2 (M+H+) 411.0406. Found: 411.0406. Anal. calcd. for CA6HR2F2N403S2 0. 5 H2O : C, 45.82 ; H, 3.12 ; N, 13.36 ; S, 15.29. Found: C, 45.78 ; H, 3.12 ; N, 13.18 ; S, 15.50.

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/72070; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 134575-14-7, name is exo-Benzyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate, 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 134575-14-7, name: exo-Benzyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

24.2. (la,5a,6a)-6-Formyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester:DMP (15% in DCM, 20 mL) was added to a solution of intermediate 24.1 (1.27 g) in DCM (20 mL) at RT. After stirring for 2h40 at RT, sat. aq. NaHCO3 was added and the phases were separated. The org. phase was dried (MgSO^ and evaporated off. CC (Hept/EA 12/88 to EA) of the crude afforded 620 mg of the desired compound as orange oil.LC-MS: tR = 0.86 min; [M+H]+: 246.04.

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; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; HILPERT, Kurt; HUBLER, Francis; MEYER, Emmanuel; RENNEBERG, Dorte; WO2010/116328; (2010); A2;,
Amide – Wikipedia,
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