Tag: M.W=200-300

1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 1103234-56-5

Example 1; Step a; Formation of Carboxylic Acid Chloride (Step a) 1) According to Scheme 1); 55.8 g Sulfonamide Acid (2) was placed into a dried 1st reaction vessel kept under nitrogen atmosphere, to which 280 mL methylenchloride were added. Then 619 muL DMF were added to the obtained suspension and the resulting mixture was kept at a temperature between 18-22 C. Then, 25.4 g oxalylchloride were dissolved in 66 mL methylenchloride, and this solution was slowly added over approximately 30 minutes to the above-mentioned suspension whereby the temperature of said suspension was kept between 18-22 C. The formation of CO2 and CO could be observed during said addition. The reaction mixture was then further stirred for about 4 to 6 hours and further kept at a temperature between 18-22 C. until the suspension almost entirely turned into a solution and no gas formation could be observed any more.

Statistics shows that 1103234-56-5 is playing an increasingly important role. we look forward to future research findings about 2,6-Difluoro-3-(propylsulfonamido)benzoic acid.

Reference:
Patent; Hildbrand, Stefan; Mair, Hans-Juergen; Radinov, Roumen Nikolaev; Ren, Yi; Wright, James Anderson; US2011/28511; (2011); 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. 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., 1103234-56-5

3H-Imidazo[4,5-b]pyridin-6-amine (29 mg, 0.22 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (60 mg, 0.22 mmol, 1 eq.), EDCI (46 mg, 0.24 mmol, 1.1 eq.), and 1-hydroxybenzotriazole (“HOBT”)eta2O (33 mg, 0.22 mmol, 1 eq.) were combined in dry DMF (2 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine and extracted with ethyl acetate (“EtOAc”; 2 X). The extracts were washed with water (1 X), dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by preparative TLC (2 X 0.5 mm plates, 10% MeOH/DCM) to give 2,6-difluoro-N-(3H-imidazo[4,5-b]pyridin-6-yl)-3-(propylsulfonamido)benzamide (7.4 mg, 9%). 1H NMR (400 MHz, DMSOd6) delta 12.63 (br s, IH), 11.03 (br s, IH), 9.81 (br s, IH), 8.43-8.53 (m, 3H), 7.53-7.59 (m, IH), 7.26-7.30 (m, IH), 3.11-3.15 (m, 2H), 1.74-1.80 (m, 2H), 0.98-1.02 (m, 3H); m/z (APCI-pos) M+l = 394.3.

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; ARRAY BIOPHARMA INC.; GENENTECH, INC.; WO2009/111277; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6269-91-6, 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. 6269-91-6 name is 2-Methyl-5-nitrobenzenesulfonamide, 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.

To a stirred solution of 2-methyl-5-nitrobenzenesulfonamide (4.6 g, 0.021 mol) in 2-methoxyethyl ether (43 mL), at 0¡ã C., was added a solution of 16.1 g of tin(II) chloride in 32 mL of concentrated HCl dropwise over 15 min. After the addition was complete, the ice bath was removed and the solution was allowed to stir for an additional 30 min. Approximately 130 mL of diethyl ether was added to reaction. The mixture was stirred vigorously for 1 h. The mixture was basified with a solution of NaOH and NaHCO3, and extracted with ethyl acetate (*3). The combined ethyl acetate layers were dried over anhydrous MgSO4, filtered and concentrated to give crude product. Trituation of the crude product with methanol provided 2.4 g of pure 5-amino-2-methylbenzenesulfonamide as light brown solid. 1H NMR (300 MHz, DMSO-d6) delta 7.11-7.10 (m, 3H), 6.95 (d, J=8.1 Hz, 1H), 6.60 (dd, J=8.1 and 2.4 Hz, 1H), 5.24 (s, 2H), 2.36 (s, 3H). MS (ES+, m/z) 187 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-5-nitrobenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; US2008/293691; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, 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. 6292-59-7 name is 4-(tert-Butyl)benzenesulfonamide, 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.

Example 3: Preparation of 4-tert-Butyl-N-[6-chloro5-(2-methoxyphenoxy) [2,2]- bipyrimidinyl-4-yl] -benzene sulfonamide compound of formula-4.p-t-butyl benzene sulphonamide (2.2g,0.0104mol) was taken in Dimethyl Sulphoxide and potassium carbonate was added (2.75g,0.0198mol) under inter atmosphere and stirred for 0.5h. 3.4g of 4,6- dichloro 5-(2-methoxyphenoxy) [2,2]-bipyrimidinyl compound (formula-3) 3.44g, 0.009mol was added and heated to 120¡ãC and maintained at the same temperature for 2h. The reaction mass was quenched in IN hydrochloric acid and stirred for 2h. Product precipitates out and was filtered and washed with water and dried under vacuum yielding 4.3g(96percent) of pale yellow crystalline solid 4,6- dichloro 5-(2-methoxyphenoxy) [2,2]- bipyrimidinyl compound of formula-3 having the X-ray diffraction pattern with peaks at 8.547, 9.867, 11.068, 11.97, 13.851, 14.726, 15.539, 17.213, 18.428, 20.463, 22.232, 22.704, 23.536, 23.937, 24.827, 26.291, 26.545, 27.294, 27.815, 28.223, 29.278, 30.022, 30.5, 31.447, 31.996, 32.454, 33.43, 33.644, 34.251, 34.89, 35.662, 36.393, 37.402, 38.523, 39.022, 40.238, 40.724, 41.35, 41.93, 43.732, 44.289, 45.24, 47.267, 47.978, 49.123, 49.438, 50.22, ¡À 0.2 degrees two theta values.This was optionally purified using acetonitrile under the reflux condition to give pure pale yellow to off white crystalline product for formula-4 having the XRD.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(tert-Butyl)benzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; BIOCON LIMITED; VENKATA, Srinivas, Pullela; KOTHAKONDA, Kiran, Kumar; RAJMAHENDRA, Shanmughasamy; CHANDRASEKARAN, Indrajit; KALIAPPAN, Mariappan; MAILAR, Rekha, Shivappa; WO2013/57545; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2, A common compound: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 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: To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and Imatinib- COOH (54 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 0.1 mmol, 1 eq) and DIPEA (48 mircoL) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the reside was dissolved in DCM (1 mL) and treated with a solution of anhydrous HC1 in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid.L). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid. Analytical data (HRMS) are provided in table V.

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, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF DUNDEE; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; CIULLI, Alessio; (279 pag.)WO2019/238886; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, 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. 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The oily mass of formula-IIId obtained in step (i) (c) is taken and dissolved in 125.0ml of n-butanol. The solution is heated to 100C under nitrogen atmosphere. A solution of 29.1gms (0.1mole) of 2-(2-ethoxyphenoxy) ethyl iodide in 30ml of n-butanol is slowly added at 100-105C over a period of 3-4 hrs and maintained at 100-110C for further 4hrs. Then n-butanol is distilled off under vacuum at temp not exceeding 80C. The resulting mass is cooled to 20C and vacuum released under nitrogen atmosphere. 50.0ml of n-hexane is added to the mixture. An uniform slurry is made and the product is allowed to solidify at 0-5C. It is filtered and washed with 50ml of n-hexane. The product is dried at 40-50C under vacuum to obtain 22.0gms solid of quarternary ammonium salt of formula-IId. Recrystallized (from acetonitrile) has the following characteristics. MR : 200-208C 1H NMR : (200MHz, DMSO-d6) delta 1.15-1.19 (d, 3H), 1.28-1.31 (t, 3H), 2.60-2.70 (m, 2H), 3.40 (broad, 2H), 3.46-3.54 (m, 3H), 3.9 (s, 3H), 3.87-4.01 (dd, 4H), 4.20- 4.22 (t, 2H), 6.92-7.67 (aromatic, 11H), 8.15 (s, imine, 1H) IR : (KBr), 3305, 3210, 2930, 1632, 1609, 1494, 1439, 1330, 1282, 1252, 1456, 1075, 1011, 533, 522, 454 cm-1

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; WO2004/16582; (2004); 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 65854-91-3 as follows. 65854-91-3

EXAMPLE 3 Preparation of 4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate. N-(4-Chlorophenyl)-2,2-dimethyl propanamide (36.7 kg, 173 mol) was charged to a solution of TMEDA (20.2 kg, 174 mol) in anhydrous t-butyl methyl ether (271.5 kg) and cooled to -20 C. To the cold slurry was added 2.7 N n-butyllithium in hexane (101.9 kg, 393 mol) while keeping the temperature below 5 C. After aging 2 hr at 0 to 5 C., the solution was cooled below -15 C. then rapidly reacted with ethyl trifluoroacetate (34.5 kg, 243 mol). After 30 min, the resulting solution was quenched into 3N HCl (196 L, 589 mol) keeping the temperature below 25 C. After removal of the aqueous phase, the organic solution was concentrated by distilling approximately 200 L of solvent. Acetic acid (352 kg) was added while distilling 325 kg solvent under 100 mm vacuum. After cooling the solution to 30 C., 12 N HCl (43.4 kg, 434 mol) was added and the mixture heated to 65 to 70 C. and held 4 hours. The resulting slurry was cooled to 5 C. and the product was collected by filtration, washed with ethyl acetate (50.5 kg) and dried in vacuo to give 42.1 kg (87%) of the title compound as a white crystalline solid: mp 159-162 dec; 1 H NMR (300 MHz, DMSO-d6) d 7.65-7.5 (complex, 2H), 7.1 (d, J=8 Hz, 1H), 7.0 (brs, 3H); 19 F NMR (282 MHz, DMSO-d6) delta-69.5.

According to the analysis of related databases, 65854-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DuPont Pharmaceuticals Company; US6028237; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, 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. 239074-29-4.

A suspension of 7-chloro-8-hydroxy-l-methyl-l,5-naphthyridin-2(lH)-one (1 g, 4.75 mmol) (for a synthesis see WO2008006648 Example l(c)) in THF (24 ml) was stirred at rt and treated with 1,1-dimethylethyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (1.089 g, 4.75 mmol, for a preparation see Example l(g)), triphenylphosphine (1.619 g, 6.17 mmol) and DIAD (1.215 ml, 6.17 mmol). The resulting yellow suspension was stirred for 30 min then heated at 8O0C for 3.5 hours. Additional triphenylphosphine (0.8 g, 3.05 mmol) and DIAD (0.6 ml, 3.05 mmol) were added and the suspension (now orange) was heated to 8O0C for 2 hours. The suspension was cooled and stirred at rt overnight. The solvent was evaporated under vacuum and to deliver an orange gum. Chromatography on silica, eluting with 0-50% DCM/CH3CN gave a white solid that contained residual triphenylphosphine oxide. Diethylether (50 mL) was added and the resulting suspension was stirred for 30 minutes, filtered under vacuum. The precipitate was dissolved in DCM, filtered and the filtrate was evaporated to give the title compound (1.16 g, 42%). MS (ES+) m/z 422 [MH+].

The synthetic route of tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4,Some common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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: A solution of 4-(Boc-aminomethyl)benzylamine (1) (1.0 mmol)and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with anice bath, then the corresponding sulfochloride (1.1 mmol, dissolvedin 2mL anhydrous DCM) was added dropwise. The reactionmixture was allowed to stir at 0 C for 1 h. After removing thecooling bath, the resulting mixture was stirred for 5 h at roomtemperature, then diluted with saturated aqueous NaHCO3 andextracted with DCM (10 mL) for three times. The combined organiclayer was sequentially washed with water and brine, dried withanhydrous Na2SO4, and concentrated in vacuo. The crude was purifiedby column chromatography with DCM/methanol (150:1, v/v)to yield the product as a white solid [5].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108468-00-4, its application will become more common.

Reference:
Article; Bai, Renren; Sun, Jian; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Oum, Yoonhyeun; Xie, Yuanyuan; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 195 – 205;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 116091-63-5, name is 2-Methoxy-5-(2-oxopropyl)benzenesulfonamide, molecular formula is C10H13NO4S, 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. 116091-63-5

Preparation of R,R-2-Methoxy-5-[2-(1-phenylethylamino)-propyl]benzenesulfonamide, hydrochloride (Formula IV) (3-sulfonamido-4-methoxyphenyl)-2-propanone obtained from Example 1 was added to methanol (300 ml) and activated Raney Ni (1.5 g) in a hydrogenation flask. R(+)-1-phenyl ethylamine (1 g) was added and hydrogen gas was applied at a pressure of 3.5 bar. Temperature was raised to 50 C. and pressure raised to 5.5. bar. The reaction mixture was cooled to room temperature and Raney Ni filtered through hyflo bed. The filtrate was concentrate under reduced pressure at 50 C. and toluene (10 ml) was added. The resultant solution was concentrated at 50-60 C. under reduced pressure to recover toluene completely and get a thick oil (3 g approx.) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116091-63-5, its application will become more common.

Reference:
Patent; Ranbaxy Laboratory Limited; US6894188; (2005); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics