Tag: M.W=200-300

Electric Literature of 16091-26-2,Some common heterocyclic compound, 16091-26-2, name is 3′-Aminobenzanilide, molecular formula is C13H12N2O, 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.

In a 250 mL three-necked flask equipped with a stirrer, a thermometer and a reflux condenser (with a water separator), 130.0 g of methyl chloroacetate was added.42.4 g of m-anilinoaniline was added under stirring.24.5 g of sodium carbonate was uniformly mixed under stirring, and the temperature was raised to 100 to 105 C, and refluxed for 2.0 h. 4.2 g of potassium bromide and 0.3 g of zinc powder were added, and the mixture was refluxed at 110 to 130 C for 3.0 h. The sample was sampled and detected by high pressure liquid chromatography, and the purity of the target product was 99.2%. After methyl chloroacetate was distilled off under reduced pressure, acetic acid was added to obtain an acetic acid solution of m-benzoylamino-N,N-di(methyl acetate) aniline in a yield of 98.4%.

The synthetic route of 16091-26-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central South University of Forestry and Technology; Zhao Ying; Hu Renjie; Xiong Yuanfu; Zhao Qi; Yuan Yao; Tan Xiaoyan; (8 pag.)CN109796365; (2019); A;,
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Reference of 121-30-2, A common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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.

To a solution of 2,4-disulfamyl-5-chloroaniline (15c, 3 g, 10 mmol) in acetonitrile (120 mL) at 40 C was slowly added concd sulfuric acid (13.5 mL). After 30 min, to the solution was added sodium nitrite (1.32 g, 19.1 mmol) portionwise. The solution was stirred at 0 C for 1 h, to which was then added a solution of CuBr2 (2.46 g, 11 mmol) in water (2 mL) in portions. After 1.5 h, the reaction mixture was warmed to room temperature and then heated to 80 C to evolve nitrogen gas. When no further gas was generated, the solution was concentrated. Purification by flash column chromatography on a silica gel column with hexane/EtOAc (1:1) provided a pale yellowish solid 16c in 62% yield. Mp 291-292 C (lit:refPreviewPlaceHolder25 290 C). 1H NMR (400 MHz, acetone-d6) delta 8.67 (s, 1H; ArH), 8.36 (s, 1H; ArH), 7.03 (br, 4 H; SO2NH2). 13C NMR (100 MHz, acetone-d6) delta 145.0, 144.1, 140.7, 134.0, 128.8, 96.7.

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; Tan, Chen-Ming; Chen, Grace Shiahuy; Chen, Chien-Shu; Chang, Pei-Teh; Chern, Ji-Wang; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6316 – 6328;,
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Reference of 53297-68-0, A common heterocyclic compound, 53297-68-0, name is 2-Chloro-4-sulfamoylaniline, molecular formula is C6H7ClN2O2S, 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.

To a solution of the carboxylic acid and aniline shown above, in pyridine at O0C, was added POCl3 dropwise for 5 min. The reaction was complete after stirring at O0C for an additional 50 min. The reaction mixture was quenched by addition Of H2O (1 mL), then concentrated in vacuo to light brown oil which was diluted with CH2Cl2 (200 ml). The organic layer was washed with H2O (1 x 50 ml), saturated NaHCO3 solution (1 x 50 ml), then brine (1 x 50 ml). The organic solution was dried over Na2SO4 and concentrated to dryness. The resulting oil was triturated with EtOH to give light yellow solid. To the mixture was added H2O to collect more solid. The light yellow solid was collected by vacuum filtration and dried under high vacuum for 16 hrs to yield 930 mg (72%) of product. Additional product (132 mg, 10%) was recovered by extraction of the filtrate with CH2Cl2 followed by column chromatography with acetone/CH2Cl2 (20:80).

The synthetic route of 53297-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/26356; (2006); A2;,
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Reference of 147291-66-5, These common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, 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.

10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 155 mg, 0.55 mmol), tert-butyl N-[(3-aminophenyl)methyl]carbamate (Chembasics, 111 mg, 0.50 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27 mg, 0.05 mmol) were dissolved in 1,4-dioxane (7.5 mL) Caesium carbonate (326 mg, 1.0 mmol) was added and the mixture purged with a stream of nitrogen for 5 minutes.Tris(dibenzylideneacetone) palladium (II) (28 mg, 0.03 mmol) was added and the apparatus was evacuated and backfilled with nitrogen (×3) and then heated at 100 C. for 8 h. The mixture was cooled, filtered and the filtrate absorbed onto an SCX-3 column, washed with methanol and the product eluted with ammonia in methanol. Product containing fractions were concentrated and purified by normal phase chromatography (1% methanol/DCM) to give the title compound as a white solid (57 mg, 24%).1H NMR (399.9 MHz, DMSO-d6) delta1.41 (9H, s), 1.59-1.71 (6H, m), 1.96 (2H, m), 2.58 (2H, m), 3.17 (3H, s), 3.61 (2H, m), 4.09 (2H, d), 4.85 (1H, m), 6.80 (1H, d), 7.18 (1H, t), 7.30 (1H, t), 7.57 (1H, d), 7.62 (1H, s), 8.04 (1H, s), 9.16 (1H, s); MS m/z 467 [M+H]+.

Statistics shows that tert-Butyl 3-aminobenzylcarbamate is playing an increasingly important role. we look forward to future research findings about 147291-66-5.

Reference:
Patent; ASTRAZENECA AB; US2008/9482; (2008); 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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 456-64-4

Compound 60; N-phenytrifluoromethanesulfonimide (3.336 g, 9.337 mmol, 1.1 eq.) was added to Compound 53 (2.37 g, 8.488 inmol, 1.0 eq.) in 100 mL DCM, followed by Cs2CO3 (3.04 g, 1.1 eq.). The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered through CELITE and concentrated. The residue was purified by silica gel chromatography (30-60% EtOAc/hexane) to give Compound 60 as the white solid (3.2 g, 92%). 1H NMR (300 MHz, CDCl3): delta 7.37 (d, 2 H), 7.20 (d, 2 H), 4.50 (m, 1 H), 4.18 (m, 1 H), 3.03 (m, 1 H), 2.98 (m, 2 H), 2.85 (m, 1 H), 2.62 (m, 1 H), 1.39 (s, 9 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; GILEAD SCIENCES, INC.; WO2008/11117; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 88829-82-7, name is tert-Butyl (8-aminooctyl)carbamate, 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 88829-82-7, category: amides-buliding-blocks

To a solution of 2-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H- benzo[de]isoquinolin-5-yloxy)acetic acid (80 mg, 0.21 mmol) and tert-butyl 8- aminooctylcarbamate (51 mg, 0.21 mmol) in DMF (1 mL), DIEA (136 mg, 1.05 mmol) and HATU (160 mg, 0.42 mmol) were added at room temperature. After 10 mins, the reaction mixture was quenched with water, extracted with EtOAc (5 mL * 3). The organic layer was concentrated under vacuum. The resulted residue was purified with flash chromatography to yield tert-butyl 8-(2-(2- (2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-5- yloxy)acetamido)octylcarbamate (109 mg, 0.18 mmol, 88%). (0282) [0228] LC/MS m/z calculated for [M+H]+ 609.3, found 609.3.

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; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael; ZHANG, Tinghu; FISCHER, Eric; VERANO, Alyssa; HE, Zhixiang; DU, Guangyan; DONOVAN, Katherine; NOWAK, Radoslaw; YUAN, Christine; (0 pag.)WO2020/6262; (2020); A1;,
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Synthetic Route of 144-80-9, These common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, 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: Two to three drops of conc. H2SO4 (8-9 mmol) was added to a solution of sulpha drug (3 mmol) and water (5 mL) and kept on an ice bath. A cold solution of NaNO2 (0.207 g, 3 mmol) was added drop-wise to it by maintaining the temperature of the reaction up to 5C. After completion of addition, the solution was kept for 15 min with occasional stirring to complete the diazotization reaction. To the ice cold solution of a above prepared Schiff?s base (3 mmol) with ethanol and 10% of 20 mL of aqueous NaOH, individual diazotised sulpha drugs was poured. The resultant mixture was stirred and allowed to stand in an ice bath for 1 h and the pH was maintained at 5-6 by occasional and controlled addition of dilute HCl. Then the coloured products obtained were filtered, washed repeatedly with water and dried. The progress of reaction was monitored by TLC using suitable solvent system ethyl acetate and cyclohexanol. Finally the products were purified by recrystallization from ethanol.

Statistics shows that N-((4-Aminophenyl)sulfonyl)acetamide is playing an increasingly important role. we look forward to future research findings about 144-80-9.

Reference:
Article; Sarangi, Priyambada Kshiroda Nandini; Sahoo, Jyotirmaya; Behera, Somalisa; Paidesetty, Sudhir Kumar; Mohanta, Guru Prasad; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 56B; (2017); p. 1256 – 1264;,
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Application of 99733-18-3, 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. 99733-18-3, name is tert-Butyl (7-aminoheptyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(4-((5-(((5-(/tvV-butyl (oxazol-2-yl (methyl (thio)thiazol -2- yl)carbamoyl)piperidin-l-yl)acetic acid (200 mg, 0. 46 mmol) in DMF (5 mL) was added tert- butyl (7-aminoheptyl)carbamate (126 mg, 0.55 mmol) and DIEA (118 mg, 0.92 mmol), followed by HOBt (93 mg, 0.69 mmol) and EDCTHCl (133 mg, 0.69 mmol). After overnight at RT, the mixture was diluted with H2O and extracted with EA. The combined organic layers were washed with saturated NaHC03, dried over Na2S04, filtered and concentrated to give the crude product, which was purified using silica gel eluting with MeOH/DCM (0% to 10%) to give /c/V-butyl (7- (2-(4-((5-(((5-(/er/-butyl)oxazol-2-yl)methyl)thio)thiazol-2-yl)carbamoyl)piperidin-l- yl)acetamido)heptyl)carbamate (243 mg, 82% yield) as a solid. MS (ESI) m/z 651.2 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (7-aminoheptyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOTHERYX, INC.; CHAN, Kyle W.H.; CHOURASIA, Aparajita Hoskote; ERDMAN, Paul E.; FUNG, Leah; HECHT, David Aaron; MERCURIO, Frank; SULLIVAN, Robert; VACCA, Joseph P.; (156 pag.)WO2020/23782; (2020); 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. 60041-89-6, name is 2-Amino-5-fluoro-N-phenylbenzamide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C13H11FN2O

[415] To a 0 °C stirred mixture of 2-amino-5-fluoro-N-phenylbenzamide (1.0 g, 4.35 mmol) and (2iS)-2-(teri-butoxycarbonylamino)propanoic acid (987 mg, 5.22 mmol) in DCM (8 mL) were added DIPEA (1.5 mL, 8.6 mmol) and HATU (1.99 g, 5.23 mmol), the mixture was stirred at 45 °C overnight. Water (30 mL) was added to the above mixture, and the resulting mixture was extracted with EtOAc (50 mL chi 2). The combined organic phases were concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1) to give the title compound as an off-white solid (1.6 g, 92.0percent). MS (ESI, neg. ion) m/z: 400.2 [M-H]”; NMR (400 MHz, DMSO-<) delta (ppm): 1 1.08 (s, 1H), 10.49 (s, 1H), 8.47 (dd, J = 9.1, 5.3 Hz, 1H), 7.73 (d, J= 7.7 Hz, 3H), 7.52 (d, J = 6.5 Hz, 1H), 7.44 (td, J = 8.8, 3.0 Hz, 1H), 7.36 (t, J = 7.9 Hz, 2H), 7.15 (t, J = 7.4 Hz, 1H), 4.08-3.93 (m, 1H), 1.30 (s, 9 H), 1.28-1.27 (d, J=4.0 Hz, 3 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 60041-89-6. Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; WANG, Tingjin; FENG, Xuejin; WU, Shuang; ZHANG, Tao; WANG, Liang; (139 pag.)WO2016/149160; (2016); A1;,
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These common heterocyclic compound, 61436-88-2, name is 2-Bromo-N-methylbenzamide, 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: C8H8BrNO

Taking R = CH3 as an example, under the protection of nitrogen, the product 2-bromo-N-methylbenzamide (0.214 g, 1 mmol) obtained in step 1,Pd (PPh3) 4 (60mg, 0.05mmol), CsF (0.456g, 3mmol) dissolved in a mixture of 15mL of 1,4 dioxane and 8mL of water, Slowly add 10 mL of a 1,4-dioxane solution containing 2-formylphenylboronic acid (0.3 g, 2 mmol),Then the reaction was terminated at 80 C. for 18-24 hours. After the reaction solution was cooled to room temperature, it was extracted twice with ethyl acetate (40 mL × 2).The organic phase was collected, washed twice with saturated brine (40 mL × 2), and then dried over anhydrous sodium sulfate.A white solid was separated by flash chromatography, and 0.2 g of white crystals were obtained after recrystallization from acetonitrile with a yield of 83%.

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

Reference:
Patent; Chinese Academy Of Sciences Fujian Structure Of Matter Institute; You Lei; Zha Daijun; (18 pag.)CN110734387; (2020); A;,
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