Amides-buliding-blocks

402-46-0, 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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below.

Step 1. A mixture of 4-fluorobenzenesulfonamide (1 equiv.), tert-butyl N-(azetidin- 3-yl)carbamate (1.3 equiv.), and diisopropylethylamine (1.3 equiv.) was stirred in acetonitrile at 150 C for 1 h in a sealed vial. The reaction mixture was then concentrated and purified by silica gel chromatography using MeOH (0 – 9%) in DCM.

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Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

366-49-4,Some common heterocyclic compound, 366-49-4, name is 2-Acetamido-4-fluorotoluene, molecular formula is C9H10FNO, 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.

Example 24; Preparation of Intermediate Compound 24G; Step A – Synthesis of Compound 24B; 24A 24B; A solution of 5-fluoro-2-methylaniline (24A, 25 g, 200 mmol) in toluene (250 mL) was treated with acetic anhydride (25 mL. 226 mmol) heated at reflux for 1 hour. The reaction mixture was cooled when a colorless solid precipitated out which was filtered and washed with a mixture of ether and hexanes. The colorless solid was taken in acetic acid (150 mL) and treated dropwise with a solution of bromine (9.6 mL, 186 mmol) in acetic acid (20 mL) and stirred at rt. for 12 hours. The solution was diluted with water and the solid separating out was filtered and washed to yield N-(4-bromo-5-fluoro-2-methylphenyl)acetamide (24B, 40 g) as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Acetamido-4-fluorotoluene, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2009/32124; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 138-38-5, name is 4-Ethylbenzenesulfonamide, molecular formula is C8H11NO2S, 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. 138-38-5.

In the same manner as in Example 1, 3-(2-chloro-4-phenylbenzyl)-5-[(4-ethylbenzene)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine (213 mg) was obtained as colorless crystals from 3-(2-chloro-4-phenylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (200 mg) and (4-ethylbenzene)sulfonamide (147 mg). 1H-NMR(CDCl3): 1.22(3H, t, J=8 Hz), 2.63-2.75(5H, m), 5.62(2H, s), 6.88(1H, d, J=8 Hz), 7.29(2H, d, J=8 Hz), 7.36-7.50(4H, m), 7.60(2H, d, J=8 Hz), 7.73(1H, d, J=2 Hz), 8.01(2H, d, J=8 Hz), 8.07(1H, d, J=8 Hz), 8.11(1H, d, J=8 Hz). Mass(ESI): m/z 529 (M-1) mp: 205-206 C.

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

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6348474; (2002); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

711007-44-2, A common compound: 711007-44-2, name is 2,3-Diaminobenzamide, 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: In a dark environment, a mixture of 2,3-diaminobenzamide(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.

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, 2,3-Diaminobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Li-Jie; Yang, Kang; Li, Chun-Yu; Sun, Ya-Quan; Chemical Papers; vol. 73; 11; (2019); p. 2697 – 2705;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

107017-73-2, Name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, 107017-73-2, 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.

Step 2: tert-Butyl[1-(bromomethyl)cyclopropyl]carbamateA solution of 92.5 g of carbon tetrabromide in 150 ml of ether is added at ambient temperature to a solution of 34.5 g of the compound of the above Step 1 and 73.5 g of triphenylphosphine in 750 ml of ether. After stirring for 20 hours, the reaction mixture is filtered and concentrated. Chromatography on silica gel (dichloromethane/cyclohexane: 50/50) allows 15 g of the expected product to be obtained.

Statistics shows that tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate is playing an increasingly important role. we look forward to future research findings about 107017-73-2.

Reference:
Patent; LES LABORATOIRES SERVIER; US2010/317698; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, I believe this compound will play a more active role in future production and life. 121492-06-6

EXAMPLE 365; 5-Bromo-3-[6-(2-methylamino-ethylamino)-2-propyl-2H-pyrazolo[3,4-d]pyrimidin-4-yl]-1,3-dihydro-indol-2-one hydrochloride; salt Example 188 (50 mg, 0.123 mmol) and N-(3-aminoethyl)-N-methyl carbamic acid t-butyl ester (214 mg, 1.23 mmol) were heated in 1 mL EtOH at 130 C. in microwave for 10 min. Upon cooling, the product precipitated in the reaction tube. The resulting solid was filtered and pumped dry before stirring in 5 mL of 4N HCl/dioxane for 1 h at r.t. The reaction mixture was pumped dry, triturated in ether and filtered to afford 38 mg (65%) of a yellow solid. mp 269-271 C.; MS (ES+calculated: 444.34; found: 444.63, 445.75 M+H). HPLC (95%) purity, retention time 3.937 minutes-Method C); 1H NMR (400 MHz, TFA) delta 8.73 (s, 1H), 7.89 (s, 1H), 7.54 (d, J=8 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 4.4 (m, 2H), 4.31 (br s, 2H), 4.07 (m, 1H), 3.85 (m, 3H), 3.10 (br s, 2H), 2.12 (m, 2H), 1.13 (t, J=7 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 121492-06-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cephalon, Inc.; US2007/281949; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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. 112101-81-2

EXAMPLE 32 (b) By following the same procedure as in Example 32 (a), (S)(+)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide was obtained by using (S)(-)-N-acetyl-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide as the starting material. Melting point: 273-276 C. (decomposition). Elemental analysis for C10 H17 ClN2 O3 S: [alpha]D24: 6.0 (c=1.01, methanol). cl EXAMPLE 33 (a) In 120 ml of ethanol were dissolved 2.4 g of (R)(-)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide and 1.2 g of 2-(o-ethoxyphenoxy)ethyl bromide, and the mixture was refluxed for 16 hours under heating. The solvent was distilled away, and after rendering alkaline the residue by the addition of 10% sodium hydroxide, and the oily material precipitated was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled away, and the residue was subjected to silica-gel column chromatography. The product was eluted with CHCl3 -methanol (9:5) to provide 1.5 g of the crude crystals of (R)(-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide, which was treated with HCl-ethanol to give a hydrochloric acid salt of (R)(-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide. Melting point: 228-230 C. Elemental analysis for C20 H29 ClN2 O5 S: [alpha]D-24: -4.0 (c=0.35, methanol).

Statistics shows that 112101-81-2 is playing an increasingly important role. we look forward to future research findings about R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4731478; (1988); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 631-58-3, name is Propanethioamide, 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 631-58-3, 631-58-3

N-[5-(2-Bromo-acetyl)-4-methyl-thiazol-2-yl]-acetamide (71.6 mg) (prepared by the procedure of WO 2005/068444) is dissolved in CH3OH (5 mL) at RT, followed by addition of thiopropionamide (21.4 mg) and ammonium phosphomolybdate¡ÁH2O (37.5 mg). After completion of the reaction, water is added (25 mL) and the precipitate is filtered off to obtain the title compound as a dark green powder. Title compound: HPLC (Method F) RT 4.86 minutes; MS (Method D) M+H 268.2 and M-H 266.2.

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, Propanethioamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

177906-48-8, Adding some certain compound to certain chemical reactions, such as: 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, 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 177906-48-8.

1,3-Dibromo-2-propanol (1.70 ml, 16.5 mmol) and sodium carbonate (15.9 g, 150 mmol) were added to an ethanol (300 ml) solution of tert-butyl(trans-4-aminocyclohexyl)carbamate (3.21 g, 15.0 mmol) and the resulting mixture was stirred under heating to reflux overnight. After cooling, insoluble matter was removed by filtration through celite and then the filtrate was concentrated under reduced pressure. The residue was diluted with water, followed by extraction with ethyl acetate. Then the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (15 ml) and imidazole (2.45 g, 36.0 mmol) and tert-butyldiphenylchlorosilane (4.29 ml, 16.5 mmol) were added under ice cooling. After stirring at room temperature for 1 hour, the reaction mixture was diluted with ethyl acetate and washed with water and brine in that order. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [chloroform:methanol=10:0-4 10:1 (v/v)] to give 2.45 g (32%) of the title compound as a colorless solid.1H-NMR (400 MHz, CDCl3) delta: 1.01-1.13 (4H, m), 1.06 (9H, s), 1.46 (9H, s), 1.74-1.80 (2H, m), 1.93-2.03 (3H, m), 2.87 (2H, t, J=7.2 Hz), 3.35-3.43 (1H, m), 3.51 (2H, t, J=6.9 Hz), 4.42 (1H, t, J=6.3 Hz), 7.37-7.41 (4H, m), 7.42-7.47 (2H, m), 7.61-7.65 (4H, m).

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 177906-48-8.

Reference:
Patent; Sugimoto, Yuuichi; Uoto, Kouichi; Wakabayashi, Takanori; Miyazaki, Masaki; Setoguchi, Masaki; Taniguchi, Toru; Yoshida, Keisuke; Yamaguchi, Akitake; Yoshida, Shoko; US2012/264738; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

308283-47-8, Adding a certain compound to certain chemical reactions, such as: 308283-47-8, name is 3-Bromo-N-(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 308283-47-8.

[0288] A suspension of intermediate 50 (1.0 g, 3.42 mmol), 3 -bromo-iV- tot-butyl – benzenesulfonamide (1.28 g, 4.28 mmol), Pd2(dba)3 (30 nag, 0.03 mmol), Xantphos (40 mg, 0.07 mmol) and cesium carbonate (3.34 g, 10.24 mmol) in dioxane (50 mL) was degassed with argon for 2 min then refluxed for overnight. After cooling to room temperature, the solvent was removed by rotovap and the resulting mixture was purified by silica gel with 10percent CH3OH/CHCI3 as an eluent to afford the title compound as a white solid. The white was dissolved in hot dioxane (150 mL) and titrated with 2 M HCl in dioxane to pH 1. The solvent was removed by rotovap and the solid was recrystalized from methanol (0.15 g, 8percent).[0289] 1H NMR (500 MHz, DMSOd6): 1.08 (s, 9H), 2.20 (s, 3H), 3.0-3.2 (m, 4H), 3.7- 4.0 (m, 4H), 4.23 (s, 2H)5 7.33 (t, J= 7.9 Hz, IH), 7.38 (d, J= 7.7 Hz, IH), 7.48 (s, IH), 7.55-7.65 (m, 3H), 7.71 (d, J= 7.9 Hz, IH), 7.90 (d, J= 7.4 Hz, IH), 8.01 (s, IH), 9.96 (br s, IH)5 10.61 (br s, IH), 11.31 (br s, IH). MS (ES+): m/z 511 (M+H)+.

According to the analysis of related databases, 308283-47-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics