Category: amides-buliding-blocks

35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, 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. Quality Control of 4-(2-Aminoethyl)benzenesulfonamide

General procedure: To a cooled solution of triphosgene (1.41mmol) in THF at 0¡ãC, a mixture of primary amine (3.52mmol) and N,N-diisopropylethylamine (DIPEA, 7.04mmol) was added. The reaction mixture was stirred at the same temperature for 30min and then the other amine (3.52mmol) was added. The reaction mixture was slowly allowed to attain ambient temperature and further stirred for 8h. After the completion of the reaction, water was added to the reaction mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was subjected to column chromatography to obtain the pure compounds.

The synthetic route of 35303-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Boggu, Pulla Reddy; Sharma, Niti; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Son, Min-Jeong; Woo, Sun-Hee; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1869 – 1887;,
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Related Products of 112253-70-0,Some common heterocyclic compound, 112253-70-0, name is 2-Amino-4-bromobenzamide, molecular formula is C7H7BrN2O, 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.

Oxalyl chloride (2.9 mL, 33 mmol) was added drop wise to the mixture of compound PR-1 (5 g, 22 mmol), 2-amino-4-bromobenzamide (4.7 g, 22 mmol) and pyridine (50 mL). The mixture was stirred for 1 hour at room temperature. The solvent was removed in vacuo. The obtained residue was purified by chromatography (petroleum ether: acetate ether=5: l) resulting in a intermediate (3.6 g). Method A2; Rt: 1.15 min. m/z=:447.7 (M+Na)+ Exact mass: 425.1 The above obtained intermediate (3.6 g,), Na2C03 (2.7 g. 25.4 mmol), H20 (20 mL) and CH3CH2OH (20 mL) were stirred for 2 hours under reflux. Most of CH3CH2OH was removed in vacuo. The residue was extracted with ethyl acetate (3 x 20 mL). The organic layer was dried over Na2S04 and concentrated in vacuo. The residue was washed with t-butyl methyl ether resulting in compound QA-6 (3.4 g)

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

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2013/98313; (2013); A1;,
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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. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate, A new synthetic method of this compound is introduced below., Computed Properties of C11H14FNO2

To a solution of 4-fluorophenylcarbamic acid terf-butyl ester (1.02 g, 4.6 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (60% dispersion in mineral oil, 206 mg, 5.1 mmol). After the initial gas evolution had ceased, the reaction was allowed to stir for 15 minutes. Tetra-n-butylammonium iodide (189 mg, 0.5 mmol) was then added followed by the addition of 1-(4-chloromethyl-thiazol-2-yl)-piperidine (1.1 g, 5.1 mmol) prepared above. The mixture was heated to reflux for 1 hour. After cooling, the reaction was carefully neutralized with cold saturated sodium bicarbonate (10 ml_) and extracted with ethyl acetate (2 x 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide an oil. Flash chromatography (silica gel; 10% ethyl acetate in hexanes) provided (4-fluorophenyl)-(2-piperidin-1-yl-thiazol-4- ylmethyl)-carbamic acid te/t-butyl ester (1.25 g, 3.2 mmol) as a white solid.

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; WYETH; WO2008/73461; (2008); A2;,
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Reference of 758-96-3, A common heterocyclic compound, 758-96-3, name is N,N-Dimethylpropionamide, molecular formula is C5H11NO, 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.

Step alb: compound A5 (3-(3-methoxyphenyl)-N,N,2-trimethyl-3-oxopropanamide)To 2,2,6,6-tetramethylpiperidine (17.5 g, 125 mmol) in 50 ml dry THF were added dropwise 72 ml (115 mmol) of a n-buthyllithium solution in n-hexane (1.6 M) at -30C. After 30 minutes of stirring, 5.0 g (50 mmol) Nu,Nu-dimethylpropionamide (A1) (dissolved in 50 mL dry THF) were added and the mixture was cooled to -70C and stirred for 1 h at this temperature. 22.5 g (125 mmol) ethyl-3-methoxybenzoate (dissolved in 30 mL dry THF) were slowly added dropwise and the resulting mixture was stirred for another 2 h at -70C. After the mixture had been allowed to warm to RT, it was hydrolyzed by employing a diluted aqueous solution of HCI (36 mL). The mixture was then washed with diethyl ether several times. The combined organic layers were dried over MgS04. The organic solvents were evaporated under reduced pressure and the remaining residue was dried in vacuo. CC (eluent: n-hexane/ethyl acetate (1 :4)) yielded 6.5 g (55%) of A5 in form of a colorless oil.

The synthetic route of 758-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; BUSCHMANN, Helmut, Heinrich; HOLENZ, Joerg; WO2011/157390; (2011); A2;,
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Reference of 121-30-2,Some common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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.

1 kg of 4-amino-6-chloro-1,3-benzenedisulfonamide was mixed with 10 kg of purified water, stirred and heated to 80 C, and 0.5 kg of formaldehyde was added dropwise, and the addition was completed in about two hours. And reacted at 100 C for 0.5 hour. Cooling to 15 , adding 0.3 kg of sodium hydroxide, 0.07 kg of medicinal charcoal, 60 C stirring for 30 minutes, insulation filter. The filtrate stirring to adjust the pH value of 5.5, cooling down to 20 below the centrifugal dehydration, and with a small amount of purified water leaching, drying wet boutique. After drying crushed and packaged, the product of hydrochlorothiazide.The product was white crystalline powder and was detected by high performance liquid chromatography, which was consistent with the retention time of the main peak of the hydrochlorothiazide standard. The UV spectrum was detected at 273nm and 323nm, and the absorbance at the wavelength of 273nm was the same as that at 323nm The absorbance ratio was 5.7; consistent with the infrared absorption profile of the hydrochlorothiazide standard.The residual methanol in the product does not exceed 0.3%, the ethanol does not exceed 0.5%, the weight loss is not more than 0.5%, the ignition residue does not exceed 0.1%, the pH, chloride, heavy metal and microbial limit are in accordance with the provisions of the Chinese Pharmacopoeia 2010 edition The Calculated according to dry goods, C7H8ClN3O4S2 content of 99.2%.

The synthetic route of 121-30-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anyang Jiuzhou pharmaceutical Co., Ltd; Cao, Junhua; (4 pag.)CN103396381; (2016); B;,
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Some common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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. Recommanded Product: 141449-85-6

Example 90A 5-(6-Chloro-pyridazin-3-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid tert-butyl Ester The product of Example 6c (1.5 g, 7.1 mmol) was dissolved in 1,4-dioxane (35 mL). 3,6-Dichloropyridazine (Aldrich, 1.37 g, 9.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, Strem, 0.28 g, 0.31 mmol), 1,3-bis(2,6-di-1-propylphenyl)imidazolium chloride (Strem, 0.38 g, 0.90 mmol), and Cs2CO3 (6.97 g, 21.2 mmol) were added and the mixture was stirred at 85 C. for 18 h, then cooled to room temperature, filtered and concentrated under vacuum. The residue was triturated with 80% EtOAc-hexanes (50 mL) and the resulting solid was filtered and dried under vacuum to give 0.81 g of the title compound (2.5 mmol, 35% yield). MS (DCl/NH3) m/z 325 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 141449-85-6, its application will become more common.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 142-26-7, name is N-Acetylethanolamine, 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 142-26-7, HPLC of Formula: C4H9NO2

A mixture of the compound 37 (120 mg, 0.328 mmol), N-(2-hydroxyethyl)acetamide (50.8 mg, 0.493 mmol), N-methylmorpholine (99.7 mg, 0.985 mmol), HOBT (66.6 mg, 0.493 mmol) and DMF (5 mL) was added with EDCI in an ice-water bath, and then stirred overnight at room temperature. The reaction solution was added with water (20 mL), and extracted with ethyl acetate (15 mL¡Á3). The combined organic phase was then washed with water (15 mL) once more. After the solvent was removed by means of reduced pressure distillation, the product was purified by using a silica column (200 to 300 mesh silica gel, ethyl acetate for elution), to obtain 2-(3-cyano-4-isopropylthiophenyl)-4-methyl-selenazole-5-carboxylic acid-(2-N-acetyl)ethyl ester (79). 1H NMR (DMSO-d6, 400 MHz) delta 8.39 (d, J=2.0 Hz, 1H), 8.22-8.19 (m, 1H), 8.07-8.04 (m, 1H), 7.72 (dd, J=4.0, 8.4 Hz, 1H), 4.24 (t, J=5.2 Hz, 2H), 3.89-3.82 (m, 1H), 3.41-3.29 (m, 2H), 2.68 (s, 3H), 1.87 (s, 3H), 1.37-1.36 (m, 6H). MS (EI, m/z): 449.9 [M-H]-.

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, N-Acetylethanolamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Atom Bioscience and Pharmaceutical Co. Ltd.; SHI, Dongfang; FU, Changjin; WU, Jie; LIU, Jun; EP2927219; (2015); A1;,
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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. 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H20N2O3

Step 1t-Butyl (2-(2-aminoethoxy)ethyl)carbamate (204 mg, 1 mmol) was dissolved in saturated aq. NaHCO3 (1 0 mL). The solution was cooled to 0 C. Methyl-2,5-dioxo-2,5- dihydro-1 H-pyrrole-1 -carboxylate (155 mg, 1.0 mmol) was then added. The reaction was stirred for 1 .5 h at 0 C. The pH was adjusted to 1 -2 with 2M HCl, and the mixture was extracted with EtOAc (3 X 20 mL). The combined organic phases was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by ISCO using a 0-4% gradient of MeOH in DCM to obtain tert-butyl (2-(2-(2,5-dioxo-2,5-dihydro-1 H-pyrrol- 1 -yl)ethoxy)ethyl)carbamate. 1H NMR (400 MHz, CD3OD): 6.82 (s, 2H), 3.68 (t, J = 5.4 Hz, 2H), 3.59 (t, J = 5.4 Hz, 2H), 3.46 (t, J = 5.6 Hz, 2H), 3.1 8-3.14 (m, 2H), 1.43 (s, 9H). MS m/z 1 85.1 (M+1 -Boc). Retention time 0.918 min.

The synthetic route of 127828-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; GEIERSTANGER, Bernhard; GRUNEWALD, Jan; OU, Weijia; PAN, Shifeng; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; WO2015/189791; (2015); A1;,
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Related Products of 17193-28-1, These common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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.

General procedure: HATU (90 mg, 0.24 mmol) was added to a solution of 1g (60 mg, 0.19) in DMA (0.75 mL) at 0 C. After 20 min, tert-butylamine (20 mg, 0.28) and DIPEA (50 mg, 0.38 mmol) in DMA (0.4 mL) were added. The reaction mixture was stirred at rt for 20 hrs. The reaction mixture was quenched with aqueous TFA (4%, 0.4 mL), then, extracted with EtOAc (10 mL). The organic layer was washed with water and brine, concentrated in vacuo, then, purified by reverse phase chromatography eluted with ACN and water, and dried using lyophilization to afford the title product as white solid. ESI-MS, m/z 360 (MH)+.

The synthetic route of 17193-28-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VenatoRx Pharmaceuticals, Inc.; BURNS, Christopher J.; COBURN, Glen; LIU, Bin; YAO, Jiangchao; BENETATOS, Christopher; BOYD, Steven A.; CONDON, Stephen M.; HAIMOWITZ, Thomas; US2019/375708; (2019); A1;,
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Electric Literature of 362670-09-5,Some common heterocyclic compound, 362670-09-5, name is N1-Boc-5-methoxy-1,2-benzenediamine, molecular formula is C12H18N2O3, 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 M51 {5-Methoxy-2-[3-oxo-3-(3-pyridin-3-yl-phenyl)-propionylamino]-phenyl}-carbamic acid tert-butyl ester The title compound was prepared from (2-Amino-5-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J12) (179 mg, 0.75 mmol) and 3-oxo-3-(3-pyridin-3-yl-phenyl)-propionic acid tert-butyl ester (Example K1) (223 mg, 0.75 mmol) according to the general procedure M. Obtained as a light brown foam (256 mg). MS (ISN) 460.3 [(M-H)-].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N1-Boc-5-methoxy-1,2-benzenediamine, its application will become more common.

Reference:
Patent; Adam, Geo; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2003/166639; (2003); A1;,
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