Tag: M.W=100-200

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. 108-13-4, name is Malonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H6N2O2

EXAMPLE 3 4,6-Dihydroxy-2-trifluoromethylpyrimidine, Compound VI, starting material for Step 2 Sodium hydride (900 g, 57.5% dispersion in mineral oil; 518 g active NaH; 22.5M) was stirred with 7.5 L toluene in a 22 L round-bottomed flask. Butanol was added over 5 hr. so that the pot temperature was maintained at 40. The mixture was stirred an additional 16 hr. Malonamide (765 g; 7.5 M) was added, followed by ethyl trifluoroacetate (1065 g; 7.5 M). The ensuing reaction was exothermic; the mixture was then heated on a steam-bath for 3.5 hrs. It was then stirred at 23-25 for an additional 16 hrs. The mixture was extracted with water (1*4 L and 1*2 L). The combined aqueous extracts were treated with activated charcoal and filtered. The filtrate was maintained at 10-15 as it was acidified to pH 1-2 with 37% hydrochloric acid. The mixture was chilled to 5. The solid was isolated by filtration and dried at 50 in vacuo to give 600 g (44.4% yield) VI m.p. 255-256 (Lit. 265).

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 108-13-4.

Reference:
Patent; Bristol-Myers Squibb Co.; US4963678; (1990); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 149990-27-2, A common heterocyclic compound, 149990-27-2, name is tert-Butyl but-3-yn-1-ylcarbamate, molecular formula is C9H15NO2, 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.

A mixture of Cpd.4-5? (5.40 g, 12.9 mmol, 1.0 eq) and Cpd.2 (2.18 g, 12.9 mmol, 1.0 eq) in Et3N(110 mL) was added Cul (49.2 mg, 258 umol, 0.02 eq), PdCI2(PPh3)2 (181 mg, 258 umol, 0.02 eq) atC under N2 and stirred at 25 C for 16 hrs. TLC (petroleum ether/ethyl acetate = 1/1, Rf = 0.3) showthat the reaction was complete. Then aq.NH4CI (200 mL) was added, extracted with EtOAc (200mL*3), the combined organic layers were washed with brine, dried over Na2SO4 and filtered. Thefiltrate was concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluted with petroleum ether: EtOAc (10:1, 1:1) to give Cpd.4-6 (3.0048% yield) as yellow oil.1H NMR: ET5008-32-Plbl 400 MHz CDCI3 [17.41-7.34 (m, 1H), 7.23-7.06 (m, 3H), 4.97-4.87(m, 1H), 3.97 (s, 2H), 3.53 (t, i = 6.8 Hz, 2H), 3.43-3.33 (m, 2H), 2.72 (t, i = 8.0 Hz, 2H), 2.64 (i = 8.0 Hz,2H), 1.69-1.59 (m, 4H), 1.55-1.43 (m, 22H).

The synthetic route of 149990-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OMEICOS THERAPEUTICS GMBH; MAX DELBRUeCK-CENTRUM FUeR MOLEKULARE MEDIZIN; FISCHER, Robert; SCHUNCK, Wolf-Hagen; MUeLLER, Dominik; WESSER, Tim; KONKEL, Anne; LOSSIE, Janine; (115 pag.)WO2017/168007; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 154350-29-5,Some common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, molecular formula is C3H7NO2S, 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 6: preparation of [18-(tert-Butyl-dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester 14-tert-Butoxycarbonylamino-18-(tert-butyl-dimethyl-silanyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid (500 mg, 0.86 mmoL) was dissolved in 25 mL of THF and treated with CDI (180 mg, 1.12 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere). After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (135 mg, 1.12 mmoL) and DBU (170 mg, 1.12 mmoL). After stirring for 4 h at rt, the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and pH 4 buffer. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to give the crude product. It was then purified by flash column, eluting with 33percent ethyl acetate in hexane to isolate a white solid (300 mg, 51percent). 1H NMR (300 MHz, CD3OD) delta ppm 1H 0.07 (s, 3H), 0.08 (s, 3H), 0.85 (s, 9H), 0.87-1.49 (m, 21H), 1.73-1.95 (m, 3H), 2.08-2.16 (m, 1H), 2.25-2.36 (m, 2H), 2.42-2.56 (m, 1H), 2.85-2.93 (m, 1H), 3.65-3.74(dd, J=10.61, 3.66 Hz, 1H), 3.89 (d, J=10.25 Hz, 1H), 4.34 (m, J=9.70, 9.70 Hz, 1H), 4.43 (t, J=7.87 Hz, 1H), 4.57 (s, 1H), 4.94-5.01 (m, 1H), 5.10 (d, J=8.78 Hz, 1H), 5.66-5.75 (m, 1H), 6.55 (s, 1H), 10.13 (s, 1H). MS m/z 683 (M++1).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2009/285773; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 148017-28-1 as follows. category: amides-buliding-blocks

Step b: (2R3Ry4R,5R)-2-fr(Aminosulfonyl)(f¡ãr^-butoxycarbonyl)amino1methyl}-5-(6- cMoro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate[0462] (2R,3R,4R,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diyl di-acetate (425.0mg, 0.001146mol), N-Boc-sulf amide (337.4mg, 0.001720mol) and triphenylphosphine (360.8mg, 0.001376mol) were dissolved in ethyl acetate (10 mL) under nitrogen and diisopropyl azodicarboxylate (338.6 muL, 0.001720mol) was added dropwise as a solution in ethyl acetate (2mL). The solution was stirred at room temperature under nitrogen for 3h. The solution was concentrated in vacuo and the residue purified by flash chromatography (DCM/ EtOAc 10% to 50%) to give product, contaminated with triphenylphosphine oxide (502mg).[0463] LCMS: R.t. 1.49 min ES+ 549 (formic acid)

According to the analysis of related databases, 148017-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/84281; (2006); A1;,
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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: amides-buliding-blocks

Example 6 tert-Butyl (‘2-(7-r2-r4-cvanophenoxy>>ethyll-9-oxa-3.7-diazabicvclo[3.3.11non-3- yl } ethyDmethylcarbamateOxalyl chloride (0.544 g, 0.4 mrnol) was added at -78C to a solution of DMSO (0.7 g, 0.9 mmol) in dry dichloromethane (10 mL). The resulting mixture was EPO stirred for 15 min before tert-butyl (2-hydroxyethyl)methylcarbamate (0.5 g,0.3 mmol; prepared by reaction of 2-methylaminoethanol with di-tert-butyl dicarbonate under standard conditions, using DCM as solvent), dissolved in dry dichloromethane, was added dropwise at -78C. Stirring was continued for 3 h at the same temperature, before triethylamine was added (at -78C) and the reaction mixture was warmed to -3O0C. The reaction was quenched with citric acid solution and extracted with dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Solvent evaporation yielded (0.35 g) of crude aldehyde (tert-butyl (2-oxoethyl)methylcarbamate). The crude aldehyde was then taken in DCM (10 mL). 4-[2-(9-Oxa-3,7- diazabicyclo[3.3.1]non-3-yl)ethoxy]benzonitrile (0.221 g, 0.8 mmol; see WO 01/28992), followed by acetic acid (0.182 g, 0.3 mmol), was added. After stirring for 1 h, NaBH3CN (0.188 g, 0.3 mmol) was added. The reaction mixture was stirred at RT overnight, quenched with water and extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification by column chromatography over silica gel using 2.5% methanol in dichloromethane as eluent, yielded 80 mg of the title compound as a pale yellow, gummy liquid. 1H NMR (300 MHz, CDCl3): delta 7.58 (2H, dd), 7.00 (2H5 dd), 4.33 (2H, t) 4.20 (2H, bs), 3.79 (2H, b), 3.58 (2H, m), 3.35 (2H, d), 3.23 (2H, d), 3.1 (6H, m), 2.92 (3H5 s), 1.41(9H, s).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/135316; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 915087-25-1, These common heterocyclic compound, 915087-25-1, name is 4-Amino-2-fluoro-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.

A mixture of 4-amino-2-fluoro-N-methylbenzamide (2 g, 11.9 mmol), TMSCN (2.2 mL, 17.9 mmol), TMSOTf (0.1 mL, 0.6 mmol), and acetone (10 mL, 140 mmol) in DCM (20 mL) was stirred at room temperature overnight. The white solid was filtered, washed with a small amount of DCM, and dried to afford 1.12 g of 4-((2-cyanopropan-2-yl)amino)-2-fluoro- N-methylbenzamide as a white solid. lR NMR (300 MHz, DMSO-d6) delta 7.79 (t, 1H), 7.56 (t, 1H), 6.88 (s, 1H), 6.67 (dd, 1H), 6.54 (dd, 1H), 2.75 (d, 3H), 1.67 (s, 6H).

Statistics shows that 4-Amino-2-fluoro-N-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 915087-25-1.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2011/103202; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 5466-88-6, 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 5466-88-6 as follows.

General procedure: Phosphoric acid (3.15 g, 0.032 mol) and TFAA (21.8 mL, 0.104 mol) were added to the mixture of 4H-Benzo [1,4]oxazin-3-one (4 g, 0.026 mol) and substituted phenylacetic acid (1.1eq), at 0 C. After completion of addition, the mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was cooled to 0 C and adjusted the pH to 7 by adding the saturated NaHCO3 solution. The precipitated solid was filtered, washed with water and dried to give the desired product.

According to the analysis of related databases, 5466-88-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rajitha, Chittipaka; Dubey; Sunku, Venkataiah; Javier Piedrafita; Veeramaneni, Venugopal Rao; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4887 – 4896;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 78191-00-1, name is N-Methoxy-N-methylacetamide, 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 78191-00-1, Product Details of 78191-00-1

a) To a solution of 1-octyne in tetrahydrofuran (THF, 180 mL) previously cooled to -78 C. is added under nitrogen n-buyllithium (2.5 M solution in hexane, 33.2 mL, 83 mmol). The colorless mixture is stirred 1 h and is then treated with N-methoxy-methylacetamide in THF (20 mL). The reaction mixture is stirred at room temperature for 4 h. After that time 3M HCl solution (100 mL) is added. Tert-butyl-methyl ether (TBME) is added and the reaction mixture is extracted with TBME (3¡Á100 mL). The combined organic layers are washed with saturated NaHCO3, dried over magnesium sulphate and the volatiles are removed on rotary evaporator. The residue is then purified by flash column chromatography (eluent: ethyl acetate/hexane 1:10) to obtain product 121 (colorless oil, 6.2 g, yield: 64%). (0445) NMR: 1H (400.1 MHz, CDCl3), delta=2.35 (2H, t, J=7.2 Hz), 2.31 (3H, s), 1.57 (2H, quint., J=7.2 Hz), 1.43-1.35 (2H, m), 1.33-1.25 (4H, m), 0.89 (3H, t, J=7.0 Hz); 13C (100.1 MHz, CDCl3), delta=184.9, 94.2, 81.4, 32.7, 31.2, 28.5, 27.6, 22.4, 18.9, 14.0.

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; BASF SE; Welker, Matthias; Turbiez, Mathieu G. R.; Chebotareva, Natalia; Kirner, Hans Juerg; (74 pag.)US9550791; (2017); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1129-26-6,Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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: N-acyl-indoline 1 (0.15mmol), amide 2 (0.3mmol), [RhCp*Cl2]2 (5mol%), AgOTf (20mol%), AgOAc (20mol%), PhI(OAc)2 (0.15mmol), HOAc(0.45mmol) and DCE (1.5 mL) were added into the tube and sealed. The reaction vessel was evacuated and back filled with N2 in three times. The reaction mixture was vigorously stirred at 100 C for 16 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the desired product.

The synthetic route of 1129-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong, Yaqun; Sun, Song; Yu, Jin-tao; Cheng, Jiang; Tetrahedron Letters; vol. 60; 20; (2019); p. 1349 – 1352;,
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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H8ClNO

A solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (0.8 g, 4.1 mmol), cesium carbonate (2.0 g, 6.2 mmol), and 2-chloro-N,N-dimethylacetamide (0.47 rnL, 4.5 mmol) in DMF (14 mL) was heated in a microwave at 900C for 1 hr. The crude reaction mixtures were then diluted with water (300 mL) and extracted with ethyl acetate (3 x 50 mL). Product was purified by silica gel column using DCM/EtOAc/MeOH (8/1.5/0.5) as eluent to provide N,N-dimethyl-2-(4-(4,4,5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazol- 1 – yl)acetamide (1.3 g) as a light yellow oil. ESI-MS:m/z 280.3 (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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics