Tag: M.W=200-300

782-45-6, These common heterocyclic compound, 782-45-6, name is 4-Amino-N-phenylbenzamide, 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.

The pale yellow solid was dissolved in 20 ml of dry methylene chloride solution, c was added, a solution of triethylamine (0.07 ml) in dry dichloromethane was added dropwise and the mixture was stirred overnight at room temperature. TLC, filtration and drying were followed by treatment with 10 ml of acetic acid Ethyl acetate was heated to reflux, filtered and dried to give 0.030 g of a yellow solid with a yield of 12.5%.

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 782-45-6.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ye Fei; Tang Yanbo; Tian Jinying; Guo Zongru; Chen Zheng; Zhang Xiaolin; He Yibo; Ma Yiming; Chen Ling; Han Jing; (27 pag.)CN102382076; (2016); B;,
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42137-88-2, 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. 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

B. Dextrorotatory (+)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine. 57 g (0.2618 mole) of dextrorotatory (+)-(4-chlorophenyl)phenylmethylamine (prepared in Example 1.2) and 86.4 g (0.2917 mole) of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (prepared in Example 2.3) are added to 200 ml (1.15 mole) of ethyldiisopropylamine in a 500 ml three-necked round-bottomed flask. The mixture is heated under reflux for 3 hours, then poured in 400 ml of methanol and the mixture is cooled, in an ice bath, and stirred for 1 hour. The precipitate which forms is filtered off, washed with methanol and dried under vacuum at 50 C. 88.6 g of dextrorotatory (+)-1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine are obtained. M.P. 173.3 C. Yield: 76.7%. [alpha]D25: +43.2 (c=0.5, toluene). Optical purity: 98.35%. Analysis for C24 H25 ClN2 O2 S in %: Calc.: C 65.38 H 5.71 N 6.35 C 8.04 S 7.27 Found: 64.98 5.70 6.40 7.96 7.35

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Reference:
Patent; U C B, S.A.; US5478941; (1995); A;,
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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;,
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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;,
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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;,
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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;,
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19982-07-1, 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. 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

Add 38.9g of Compound A to a 500ml three-necked flask,The reaction bottle was placed in an ice-water bath, then 21.4ml of nitric acid was added, and then 270.4ml of sulfuric acid was slowly added, and the addition was completed in about 40 minutes. After the addition, the temperature was slowly raised to room temperature and the reaction was completed for 4h. Post-treatment: Pour the reaction solution into 1L of ice water, stir the reaction thoroughly after quenching, add dichloromethane (200ml ¡Á 5) for extraction, wash with saturated sodium chloride solution 300ml, dry with anhydrous magnesium sulfate, filter, the filtrate is reduced at 45 Autoclaved,The residue was recrystallized from ethyl acetate / n-hexane (V / V = 100ml / 100ml) at 0 C.After filtration, the filter cake was dried under vacuum (-0.09MPa) at 40 C for 3h to obtain 14.5g of product compound D. Yield: 34.8% and GC purity: 99.1%.

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; Chongqing Zhien Pharmaceutical Co., Ltd.; Chongqing Liujiang Pharmaceutical Technology Co., Ltd.; Mu Xiang; Zhang Wei; Han Juan; Li Yufang; Deng Xianglin; Xiang Yong; (9 pag.)CN110938006; (2020); A;,
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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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, A new synthetic method of this compound is introduced below., 239074-29-4

Step 2 Preparation of Ay-(3-chloro-4-fluorobenzyl)-6-(2-((frans-4-amiotanocvclohexyl)methyl)-2/-/-tetrazol- 5-yl)pyriotamiotadiotane-4-carboxamiotadelambda/-(4-Fluoro-3-chlorobenzyl)-6-(2H-tetrazol-5-yl)py?miotadiotane-4-carboxamiotade (0 71 g, 2 1 mmol) and commercially available tert-butyl frans-4-(hydroxymethyl)cyclohexylcarbamate (585 mg, 2 55 mmol) were taken up in tetrahydrofuran (20 mL) and treated with polymer supported triphenylphosphme (1 19 g, 2 55 mmol) After stirring for 30 mm at room temperature, di-tert-butyl azodicarboxylate (735 mg, 3 19 mmol) was added After 15 h at room temperature, the reaction was filtered to remove the resin The filtrate was concentrated to a crude oily residue The residue was purified via normal phase chromatography (silica, 0-75% ethyl acetate/heptane with a trace 1 % methanol ran through entire gradient) to afford the protected amine (1 08 g, 93%, 1 99 mmol) which was taken up in dichloromethane (5 mL) and treated with trifluoroacetic acid (2 0 mL, 15 mmol) After the reaction was stirred at ambient temperature for 3 h, the mixture was diluted with dichloromethane (5 mL) and neutralized with 2 5 N aqueous NaOH to achieve pH 7-8 The organic layer was separated, washed with water (3 mL), then dried over sodium sulfate, and concentrated to afford the title compound as an amber oil (0 87 g, 92%) LC/MS (5%-95% CH3CN/H2O, 6 mm) 2 24 mm, m/z 445 (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; PFIZER INC.; WO2009/16498; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4, 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of carboxylic acid (1.0 eq), amine (1.0-1.5 eq), N,N-diisopropylethylamine or triethylamine (1.5-3.0 eq) and a coupling agentsuch as HBTU (2-(1H-benzotriazol-i-yl)-i,i,3,3- tetramethyluronium hexafluorophosphate), HATU (1 -[Bis(dimethylamino)methylene]-i H-i 2,3-triazolo[4,5-b]pyridinium 3-oxidhexafluorophosphate) or HCTU (O-(i H-6-Chlorobenzotriazole-i -yl)1,1 ,3,3-tetramethyluronium hexafluorophosphate (1.0-1.5 eq) in anhydrous solvents such as DMF or DCM was stirred at room temperature for 1-72 h. The product was isolated and purified using one of the following methods: Step 4: Amide coupling of (S)-1 -[(R)-2-(tert-Butoxycarbonyl-methyl-amino)-4-phenyl- butyryl]-pyrrolidine-2-carboxylic acid (280 mg, 0.72 mmol) with 1-(N-boc-aminomethyl)-4-(aminomethyl)benzene (170 mg, 0.72 mmol) was carried out following General Method I using HATU (330 mg, 0.86 mmol) and DIPEA (0.30 mL, 1 .7 mmol) in DCM (50 mL). Purification by column chromatography (biotage, 0-80% EtOAc/petrol) gave ((R)-1-{(S)-2-[4-(tert- butoxycarbonylamino-methyl)-benzylcarbamoyl]-pyrrolidine-1 -carbonyl}-3-phenyl-propyl)-methyl-carbamic acid tert-butyl ester (230 mg, 51%) as a colourless oil.AnalpH2_MeOH_4MIN: Rt: 3.51 mi mlz 609 [M+H]

The synthetic route of 108468-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF LEEDS; PHILIPPOU, Helen; FOSTER, Richard; FISHWICK, Colin; REVILL, Charlotte; YULE, Ian; TAYLOR, Roger; NAYLOR, Alan; FALLON, Philip, Spencer; CROSBY, Stuart; HOPKINS, Anna; GUETZOYAN, Lucie, Juliette; MACNAIR, Alistair, James; STEWART, Mark, Richard; WINFIELD, Natalie, Louise; (273 pag.)WO2019/186164; (2019); A1;,
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112101-81-2, A common compound: 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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.

EXAMPLE 3;Preparation of Tamsulosin HydrochlorideTamsulosin Hydrochloride is also prepared according to this example by first repeating the initial reaction, cooling, and filtering steps of Example 2 to produce the filtrate at 0 C.Instead of using ammonia, the filtrate is then alkalinized with DIEA until a pH of 8.5 is obtained, and the desired product is extracted with 2 x 50 mL of AcOEt. The combined organic layers are then extracted twice with 50 mL of water at pH 6 (adjusted with HCl). The EPO aqueous phases are combined and the pH is again adjusted to 8.5 with DDEA, and the product is then extracted with 2 x 25 mL of AcOEt.The combined organic phases obtained from the extractions are dried over Na2SO4 and the solvent is evaporated to obtain 3.28 g of crude tamsulosin. The content of byproduct as determined by HPLC method 1 was 0.261% (area percentage).The residue is dissolved in ethanol (32 mL) and 1.65 mL (7.76 mmol) of ethanol HCl 4.7 N are charged. Then, the mixture is cooled down to 0 C and the solid is collected by filtration, washed with ethanol and dried in vacuum at 60 C until constant weight to yield 2.17 g (4.87 mmols, 26% molar yield) of tamsulosin hydrochloride. By subsequent analysis, the content of by-product (formula (VE)) by HPLC method 1 at this stage is 0.08 area %.The tamsulosin hydrochloride thus obtained is further purified by repeating twice the following procedure: treating with 29 mL of ethanol at 78 C, stirring for 30 minutes, cooling to 0 C, filtering, washing with ethanol and then drying at 60 C in vacuum until constant weight. After drying, 1.98 g of tamsulosin hydrochloride are obtained (4.45 mmols, 91% partial molar yield). (Assay: 100.21%; IR: matches the standard; melting point: 227.4-229.3 C; chemical purity: 99.31 area % by HPLC method 1; XRD (20), see Figure 1; content of byproduct (formula (VII)) by HPLC method 1 : 0.02 area %)

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, R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICHEM, S.A.; WO2007/4077; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics