Author: Jessica.F

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. 188345-71-3, name is 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, A new synthetic method of this compound is introduced below., SDS of cas: 188345-71-3

2-(Tert-butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-ene was dissolved in 200 mL of dichloromethane-methanol (2:1), and the solution was cooled to -78 C. Ozone was passed through the solution until it turned blue and then for a further 10 min. Argon was bubbled through the solution to remove excess ozone (the solution turned colorless). This process (ozone, followed by argon) was repeated one more time to ensure complete formation of the ozonide. Sodium borohydride (3.7 g, 97 mmol) was carefully added to the reaction mixture at -78 C., and the resulting mixture stirred for 16 h, as the temperature of the reaction was gradually increased to ambient. Saturated ammonium chloride solution (100 mL) was added, and the mixture was stirred for an additional 1 h. The mixture was extracted with dichloromethane (2¡Á150 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation to give 1-(tert-butoxycarbonyl)-2,4-bis(hydroxymethyl)pyrrolidine, as a light yellow oil.

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; Targacept, Inc.; US2011/263629; (2011); A1;,
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Synthetic Route of 68621-88-5, These common heterocyclic compound, 68621-88-5, name is tert-Butyl (3-aminophenyl)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.

(3-Aminophenyl)carbamic acid tert-butyl ester (1.0 g) was dissolved in ethyl acetate (30ml) and treated with aqueous formaldehyde (37% wt, 443 mul) and palladium on carbon (10%, 350 mg). The reaction mixture was hydrogen- ated under a balloon of hydrogen overnight at atmospheric pressure. The cata- lyst was removed by filtration through Celite under nitrogen and the volatiles were removed by evaporation. The residue was purified by chromatography using the Biotage system on a 10 g silica cartridge eluting with a mixture of ethyl acetate and cyclohexane (1 :19 increasing to 1 :1) to give (3-methylamino- phenyl)carbamic acid tert-butyl ester (500 mg). LCMS (Method A) Rt 2.45 (M+H+) 2231H NMR (300MHz) (CDCI3) delta 7.2 (t, 1 H) 6.8 (br s, 1H) 6.5 (dd, 1 H) 6.4 (br s, 1 H), 6.3 (dd, 1 H) 3.7 (br s, 1 H) 2.8 (s, 3H) 1.5 (s, 9H)

Statistics shows that tert-Butyl (3-aminophenyl)carbamate is playing an increasingly important role. we look forward to future research findings about 68621-88-5.

Reference:
Patent; BIOTIE THERAPIES CORP.; KORHONEN, Jani; MARJAMAeKI, Anne; NISSINEN, Liisa; PIHLAVISTO, Marjo; WO2010/146236; (2010); A1;,
Amide – Wikipedia,
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Related Products of 75175-77-8, 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 75175-77-8 as follows.

General procedure: In a 50 ml round-bottom flask, substituted enaminones (1 mmol), hydrazine hydrate (1.3 mmol) or phenyl hydrazine (1 mmol) and [crown ether MIm][HSO4] (20 mol%) were charged. The reaction mixture was stirred at 50 C under solvent-free conditions for 10-35 min. After completion of reaction (monitoredby TLC), the reaction mixture was extracted with ethyl acetate (2 9 10 ml). The extracted ethyl acetate was evaporated in a rotary evaporator and the desired product was isolated from the resultant mass by column chromatography (petether: ethyl acetate, 9.5: 0.5). Finally, the catalyst was recycled and used for thenext run.

According to the analysis of related databases, 75175-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patil, Dayanand; Chandam, Dattatraya; Mulik, Abhijeet; Jagdale, Suryabala; Patil, Prasad; Deshmukh, Madhukar; Research on Chemical Intermediates; vol. 41; 9; (2015); p. 6843 – 6858;,
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Electric Literature of 7341-96-0,Some common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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 imine (0.2mmol), rhodium acetate (0.002mmol), Molecular sieve (300 mg) and the mixture is dissolved 1.5 ml dichloromethane solvent, into mixed solution 1, in 20 C stirring for 10 minutes. Then the propargyl amide (0.24mmol) and phenyl diazonium acetic acid methyl ester (0.24mmol) dissolved in 1.0 ml methylene chloride solvent, into solution 2. The solution 2 for 20 C lower, in 1 hour for adding and mixing the solution in the injection pump 1. The reaction mixture is purified by rapid column chromatography, to obtain the pure product, its structure is shown as formula (g) is shown. The yield is 89%, dr value is equal to the 88:12. The product of the1As shown in Figure 13, H NMR schematic view thereof13C NMR schematic view as shown in Figure 14.

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

Reference:
Patent; EAST CHINA NORMAL UNIVERSITY; HU, WENHAO; WU, YONG; WANG, WENKE; TANG, MIN; (29 pag.)CN106146334; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Amino-4,6-dimethoxybenzamide

A mixture of N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide (0.770 g, 2.5 mmol), NaHSO3 (0.350 g, 3.3 mmol), and p-TsOH (0.100 g, 0.51 mmol) was added to a solution of 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.5 mmol) in DMA (20 mL). The reaction was stirred at 130 C. for 5 hours and concentrated in vacuo. The residue was diluted with H2O and saturated NaHCO3, then extracted with CH2Cl2. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, afforded the title compound (0.670 g, 56%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): delta 12.02 (s, 1H), 8.13 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 6.74 (d, J=1.9 Hz, 1H), 6.54 (d, J=2.0 Hz, 1H), 3.85-3.95 (m, 7H), 3.43-3.71 (m, 3H), 2.55-3.00 (m, 3H), 1.97-2.09 (m, 5H), 1.70-1.77 (m, 1H), 1.58-1.61 (m, 1H), 1.25-1.30 (m, 4H), 1.11-1.13 (m, 3H). ESI MS m/z 479 [M+H]+

The synthetic route of 63920-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., COA of Formula: C7H7NO4S

Pathway ii: A mixture of 4-(aminosulfonyl)benzoic acid (4)(2 mmol) and N,N,N,N-tetramethyl-O-(1H-benzotriazol-1-yl)uraniumhexafluorophosphate (HBTU) (2 mmol) in DMF(2 mL) was stirred at room temperature for 1 h. Then, a solution of the appropriate amine derivative (2 mmol) in TEA (2 mmol) was added dropwise. The reaction mixture was left overnight and then quenched with water (10 mL) and extracted with EtOAc (3 5 mL).The organic phase was dried with Na2SO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography(DCM/MeOH 96:4), crystallized by treatment with a mixtureof Et2O and EtOH (1:1) to give the desired final compounds 5b, 5c,6a, 7a-f and 8a-d as white crystals. For compounds 5 a-d, 6a, 8a and 8d registered CAS numbers have been already assigned. However,their synthetic procedures, chemical properties and structural characterization are not available in literature.

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; Buemi, Maria Rosa; Di Fiore, Anna; De Luca, Laura; Angeli, Andrea; Mancuso, Francesca; Ferro, Stefania; Monti, Simona Maria; Buonanno, Martina; Russo, Emilio; De Sarro, Giovanbattista; De Simone, Giuseppina; Supuran, Claudiu T.; Gitto, Rosaria; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 443 – 452;,
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Application of 20188-40-3,Some common heterocyclic compound, 20188-40-3, name is 4-(Aminomethyl)benzamide hydrochloride, molecular formula is C8H11ClN2O, 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.

Ethyl 2-(2-fluoro-4-propylphenoxy)-4-formylnicotinate (0.13 g) obtained in Reference Example 319 was dissolved in methanol (3 mL), 4-(aminomethyl)benzamide hydrochloride (0.082 g), acetic acid (0.024 g) and triethylamine (0.061 g) were added, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added sodium tetrahydroborate (0.15 g), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by NH silica gel chromatography (hexane-ethyl acetate), and recrystallized from ethyl acetate-ethanol to give the title compound (0.079 g). MS: [M+H]+ 420.2 1H NMR (300 MHz, DMSO-d6) delta0.93 (3H, t, J = 7.3 Hz), 1.63 (2H, sxt, J = 7.4 Hz), 2.56-2.65 (2H, m), 4.48 (2H, s), 4.76 (2H, s), 7.02-7.14 (1H, m), 7.16-7.28 (2H, m), 7.34 (2H, d, J = 5.1 Hz), 7.38 (2H, d, J = 8.3 Hz), 7.87 (2H, d, J = 8.3 Hz), 7.94 (1H, brs), 8.20 (1H, d, J = 5.1 Hz).

The synthetic route of 20188-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-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 143557-91-9, category: amides-buliding-blocks

To a stirred solution of Intermediate 63 (0.68 g, 2.98 mmol) in dry DMF (10 mL) wasadded NaH (60 % dispersion in mineral oil,120 mg, 3.00 mmol). After the mixturewas stirred for 15 mm Intermediate 26 (0.5 g, 2.29 mmol) was added as one portion. The resulting mixture was stirred at RT for 48 h. The reaction mixture was poured onto brine and extracted into EtOAc. The organic layer was washed with brine, separated, dried over MgSO4, filtered and concentrated under reducedpressure to give brown oil. The crude material was purified by Biotage Isolera chromatography (silica gel, eluting with heptane-EtOAc, 1:0 to 0:1) to afford 531 mg (54% yield) of the title compound as an off-white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 7.71 (t, J = 1.4 Hz, 2H), 7.68 – 7.63 (m, 1H), 7.53 (d, J = 1.2 Hz, 1H), 7.13 (dd, J = 2.4, 1.3 Hz, 1H), 4.75 (tt, J = 10.6, 5.9Hz, 1H), 4.34 (5, 2H), 2.53 (d, J = 1.1 Hz, 3H), 2.20- 2.00 (m, 4H), 1.93 – 1.65 (m,4H), 1.49 (5, 9H).LCMS (Analytical Method A) Rt = 1 .46 mm, MS (ESIpos): m/z = 426.05 (M+H)+.

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; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, 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.

HTP Assay of CHMO Polypeptides: (0203) Primary screening used to guide optimization was carried out in a 200 muL volume in 96-well plate high-throughput (HTP) assay protocol using cell lysates. The general HTP assay conditions were: 1-100 g/L substrate (i.e., compound (1a) or (1b)), 10-200 muL of clear cell lysate containing the engineered CHMO polypeptide, 0.05-1.0 g/L NADP cofactor, 1 g/L ketoreductase (KRED) polypeptide for cofactor recycling, 0.025-0.100 M phosphate or TEA buffer solution containing 3.5%-10% (v/v) IPA (and optionally, 1.5% acetone or 10% PEG200) co-solvent, pH 8-9, 25 C. reaction temperature and 20 h reaction time (with 200 rpm shaking). The HTP assay conditions were changed slightly over the different rounds of the directed evolution of the CHMO variant polypeptide disclosed in order to detect those variants most improved in enzyme properties. Table 4 shows the HTP assay conditions used to perform primary screening of those variant polypeptides whose improved properties were confirmed by SFP assay as summarized in Tables 2A and 2B. Rounds 1-6 assays used the amide substrate of compound (1a) and Rounds 7-16 assays used the acid substrate of compound (1b). HTP Assay Results: (0220) Representative results in the primary screening using the HTP assay for both the amide substrate (compound (10) and the acid substrate (compound (2a)) are shown below in Tables 7 and 8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; CODEXIS, INC.; Ang, Ee Lui; Alvizo, Oscar; Behrouzian, Behnaz; Clay, Michael; Collier, Steven; Eberhard, Ellen; Fu, Fan Jaslyn; Song, Shiwei; Smith, Derek; Widegren, Magnus; Wilson, Robert; Xu, Junye; Zhu, Jun; (200 pag.)US9267159; (2016); B2;,
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. 535170-20-8, name is tert-Butyl (3-amino-2,6-difluorophenyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl (3-amino-2,6-difluorophenyl)carbamate

The tert-butyl-3-amino-2,6-difluorophenylcarbamate (100 mg, 0.41 mmol) prepared at Step 3 was added and dissolved into dichloromethane solvent. 2- propane sulfonyl chloride (50 uL, 0.45 mmol) and pyridine (36 uL, 0.045mmol) were added into the reaction solution and stirred at 50C for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 94 mg of the target compound, tert-butyl-2,6-difluoro-3-(1-methylethylsulfonamido)phenylcarbamate (percentage yield: 65%), was obtained.1H NMR(400MHz, CDCl3): delta 7.43(td, J = 8.8, 5.6 Hz, 1H), 6.97(bs, 1H), 6.90(td, J = 8.8, 1.6 Hz, 1H) 6.33(bs, 1H), 3.25(m, 1H), 1.49(s, 9H), 1.39(d, J = 6.8 Hz, 6H).

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 535170-20-8.

Reference:
Patent; Youai Co., Ltd.; SHIM, Eun Kyong; KIM, Nam Doo; SHIM, Tae Bo; KIM, Seung Yong; EP2647637; (2013); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics