Author: tianli

6292-59-7, Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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 6292-59-7.

General procedure: Sulfonamide 10a (2.0 g, 6.2 mmol, 1.1 eq) was solvedin dry THF (8 ml) and cooled to 78 ¡ãC under a nitrogen atmosphere.n-BuLi (1.62 N solution in hexane, 7.70 ml, 2.2 eq) wasadded drop-wise. After the addition was completed, the solutionwas stirred for 15 min, then the temperaturewas allowed to raise at60 ¡ãC and the THF was evaporated under very high vacuum. DMFwas added (10 ml), followed by dichloropyrimidine intermediate 9(2.0 g, 5.7 mmol, 1.0 eq) and the mixture was stirred overnight at50 ¡ãC. The reaction mixture was poured onto a 1:1 mixture ofwater-ice and the aqueous phase was washed with DEE, thenacidified with HCl and the resulting precipitate was filtrated off,washed with water and dried at 110 ¡ãC to afford a bright yellowsolid (2.22 g, yield 61.2percent).

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lepri, Susan; Goracci, Laura; Valeri, Aurora; Cruciani, Gabriele; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 658 – 670;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

177906-48-8, 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 177906-48-8 as follows.

Example 40 {4-[3-(6-Bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester A mixture of 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine (from Example 38 supra) (1.94 g, 6.27 mmol), trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1.61 g, 7.52 mmol), K2CO3 (1.04 g, 7.52 mmol) in DMF (20 mL) was stirred at 140 C. for 15 hours. The solution was then cooled to room temperature and poured into water. The resulted solid was filtered and washed with water. The crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1) to give {4-[3-(6-bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 0.512 g, 17%). LC-MS: [M+H]+ 487.

According to the analysis of related databases, trans-N-Boc-1,4-cyclohexanediamine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luk, Kin-Chun; Soth, Michael; US2012/238564; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 7803-58-9, name is Sulfuric diamide, 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. 7803-58-9

The preparation of sulfamide 16.1 is starting with commercially available, literature or readily available diamine. The treatment of diamine 16.1 with sulfamine a under refluxing pyridine affords sulfamine 16.3, which is followed by alkylation of [A-HALO] alkyl ester to give compound 16.4. Basic hydrolysis (LiOH, [H20/THF/MEOH)] of ester gives acid 16.1 as the intermediateds for example 61.

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 7803-58-9.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2003/106405; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

830-43-3, A common compound: 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, 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.

General procedure: All solid chemicals used were dried in vacuum over P2O5 overnight.The acid derivative and CDI were dissolved in dry THF underN2 atmosphere and the mixture was allowed to stir at 66-68 C for2 h. The sulfonamide and DBU dissolved in THF were added to thereaction mixture and stirring was continued at room temperature(4 h-overnight).Method B1: The solvent was removed in vacuo, water was addedand pH was adjusted to 2 by addition of 1 M HCl aq. The aqueousphase was extracted with EtOAc (2 40 ml), dried with MgSO4, filteredand evaporated in vacuo. For most of the compounds, a silicagel column was first run, followed by purification on aluminumoxide.

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-(Trifluoromethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Belfrage, Anna Karin; Abdurakhmanov, Eldar; Akerblom, Eva; Brandt, Peter; Oshalim, Anna; Gising, Johan; Skogh, Anna; Neyts, Johan; Danielson, U. Helena; Sandstroem, Anja; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2603 – 2620;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 630-22-8, name is 2,2-Dimethylpropanethioamide, molecular formula is C5H11NS, 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. 630-22-8.

Intermediate 23: 2-Propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate; To a solution of 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate (30 g, 85.9 mmol) (Intermediate 20) in DMA (300 mL), NBS (15.3 g, 85.9 mmol) was added. The reaction mixture was stirred at rt for 1 h. Then 2,2-dimethylpropanethioamide (11.0 g, 94.5 mmol) was added at 0 C. The mixture was stirred at rt for 2 h. The mixture was poured into water and extracted with EtOAc (200 mL¡Á3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (DCM:petroleum ether 2:1) to afford the title compound. (11 g, 35.4% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.29 (d, J=5.27 Hz, 1H), 8.12-8.19 (m, 1H), 7.12-7.25 (m, 2H), 6.80-6.88 (m, 2H), 5.85-5.98 (m, 1H), 5.20-5.37 (m, 2H), 4.61-4.67 (m, 2H). MS (ES+): 447 [M+H]+.

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

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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. 2832-19-1, name is 2-Chloro-N-(hydroxymethyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., 2832-19-1

(d) 2-Nicotinyl-4-tert-butyl-6-(N-alpha-chloroacetoaminomethyl)phenol 450 mg of the compound obtained in Example 3 (c) above was dissolved in 2 ml of a mixed solvent of acetic acid: sulfuric acid (1:1 by volume), and 330 mg of N-hydroxymethyl alpha-chloroacetamide was added to the solution. The mixture was then stirred at 60 C. for 2 hours and at 80 C. for 1 hour and poured into water. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed successively with water and an aqueous sodium chloride solution, dried and concentrated. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride: ethyl acetate (5:1 by volume) to obtain 390 mg of the title compound having the following physical properties. TLC (methylene chloride: ethyl acetate=1:2): Rf=0.30. IR (chloroform solution): nu=3430, 2960, 1670, 1630, 1590, 1530, 1460, 1415, 1370, 1345, 1275, 1250, 1130, 1100, 1055, 1020, 995 cm-1. NMR (CDCl3 solution): delta=12.10 (1H, s), 8.47-8.85 (2H, m), 7.70-8.00 (1H, m), 7.10-7.60 (4H, m), 4.48 (2H, d, J=6 Hz), 3.98 (2H, s), 1.23 (9H, s). MS: m/e=360 (M+).

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; Ono Pharmaceutical Co., Ltd.; US4245099; (1981); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 283173-80-8, name is 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, 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 283173-80-8, 283173-80-8

2-Bromo-8-fluoro-4,5-dihydro-lH-azepino[5,4,3-cd]indol-6(3H)-one (10 g; 35.3 mmol), prepared according to process described in Example 3, is charged into a three-necked round bottom flask. Potassium carbonate (4.88 g; 35.3 mmol) and bis(triphenylphosphine)palladium(II) diacetate (1.06 g; 1.41 mmol) are also charged and the flask is closed with septum seals, followed by inertisation with Ar. A previously degassed mixture of ethanol (200 mL) and water (40 mL) is added through septum seals, followed by addition of (4-((methylamino)methyl)phenyl)boronic acid solution (70 ml; 42.4 mmol), prepared according to process described in Example 1. The reaction mixture is stirred at 60C for 17 hours. The reaction mixture is cooled to ambient temperature followed by addition of activated carbon. The mixture is stirred at ambient temperature for two hours, heated to 50C, stirred for another two hours and then filtered through a layer of celite. The filter cake is washed with ethanol until the passing solvent loses yellow coloration. The yellow mother liquor is concentrated to about 80 mL. A solution of ethanol, water and cone. HCl is prepared (7V ethanol, 12V H20, 4V cone. HCl) and added dropwise while stirring at ambient temperature. The yellow suspension is left stirring for 17 hours. The suspension is cooled to 0C and stirred for one hour before filtration. The yellow Rucaparib hydrochloride is washed with water and dried in a vacuum dryer at 50C until constant mass. The solids are then suspended in dichloromethane (5V) and stirred at reflux temperature for 5 minutes, cooled to ambient temperature and then to 0C. The suspension is stirred at 0C for an hour and then filtered; the solids are washed with dichloromethane. Rucaparib hydrochloride is then dried in vacuum oven at 50C until constant mass (12.0 g). XRPD is given in Figure 1.

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, 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASSIA CHEMICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; SAMEC, Dijana Skalec; DOGAN, Jasna; BILJAN, Tomislav; SKUGOR, Maja Matanovic; MIHOVILOVIC, Moris; MUNDORFER, Tina; JANTON, Nikolina; TUKSAR, Mihaela; PIPERCIC, Sara Morasi; BAUS, Nea; (104 pag.)WO2018/140377; (2018); 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 2675-89-0 as follows. 2675-89-0

General procedure: To a suspension of NaH (344 mg, 60% dispersion in mineral oil) in THF (17 mL) was added allyl alcohol (2) (500 mg, 8.6 mmol) at 0 C. After 1 h at the same temperature, chloroacetamide 1 (0.97 mL, 9.5 mmol) was added and the mixture was stirred for 24 h. The mixture was quenched with saturated aqueous NH4Cl and concentrated at reduced pressure. The resulting residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexanes/EtOAc, 3:1) to give 6a (1.05 g, pale yellow oil) in 85% yield.

According to the analysis of related databases, 2675-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yun, Jeong In; Kim, Hyoung Rae; Kim, Sang Kyum; Kim, Deukjoon; Lee, Jongkook; Tetrahedron; vol. 68; 4; (2012); p. 1177 – 1184;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7341-96-0 name is Propiolamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of imine (0.24 mmol), rhodium acetate (0.0024 mmol) and molecular sieves (300 mg) were mixed in a 10 mL one-Oil pump for nitrogen ventilation,A 1 mL syringe was added with 1 mL of re-evaporated CH2 Cl2 Prepared as a mixed solution A and stirred at room temperature for 10 minutes.The aryl diazonium compound (0.2 mmol) and the amide compound (0.2 mmol) were dissolved in 1 mL of re-evaporated CH2Cl2 Prepared into solution B. Solution B was added to the mixed solution A at 25 C with a syringe pump over 1 hour.Stirring 3 to 12 hours,The reaction mixture was purified by column chromatography to give pure product as shown in formula (j)Methyl (2S, 3S) -3- (2-formylmethyl) -3 – ((2-hydroxyphenyl) amino) -2-phenyl-2-propiolamide propionate,The yield was 40%Dr value equal to> 95: 5,HPLC purity was 97%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Propiolamide, and friends who are interested can also refer to it.

Reference:
Patent; East China Normal University; Liu Shunying; Lei Ruirui; Jia Kaili; Wu Yong; Liu Donglan; Dong Suzhen; Hu Wenhao; (42 pag.)CN106831474; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

588-46-5, Adding some certain compound to certain chemical reactions, such as: 588-46-5, name is N-Benzylacetamide, 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 588-46-5.

General procedure: Amide 1 (0.25 mmol, 1 equiv.) and Selectfluor (0.625 mmol, 2.5 equiv.) were dissolved in acetonitrile (5 mL) at room temperature, and CuBr (0.3 mmol, 1.2 equiv.) was added over a 40 min period in 6 portions. After all the CuBr was added, the resulting mixture was stirred for extra 20 min, and then acetonitrile was evaporated under reduced pressure. Saturated ammonium chloride solution (20 mL) was added into reaction mixture and extracted with diethyl ether (25 mL ¡Á 4); the ether layers were combined and dried over Na2SO4, filtered, evaporated under reduced pressure to give the crude product. Silica gel flash chromatography of the crude product [hexanes-ethyl acetate (10:1) to hexanes-ethyl acetate (4:1)] yielded pure imide 2.

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 588-46-5.

Reference:
Article; Jin, Zhuang; Xu, Bo; Hammond, Gerald B.; Dimagno, Stephen G.; Journal of Fluorine Chemistry; vol. 143; (2012); p. 226 – 230,5;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics