Month: August 2021

127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, 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. COA of Formula: C12H12N2O2S

To a suspension of 2,4-bis(methylthio)pyrido[4,3-d]pyrimidin-5(6H)-one (150 mg, 0.627 mmol) in isopropanol (4 mL) were added 4-amino-N-phenylbenzenesulfonamide (327 mg, 1.316 mmol) and 2 drops of conc. HCl, and the reaction mixture was stirred at reflux for 10 hours. The reaction mixture was cooled, diluted with MeOH (10 mL) and treated with aqueous NaHCO3 solution to adjust pH to 7. The precipitate was collected by filtration and washed with water, and purified using column chromatography (silica gel, 0 to 80% 3:1 DCM:MeOH/DCM) to give 190 mg of product as a pale brown solid. MS (ES) m/z = 440.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 2.53 (s, 3H), 6.36 (d, J = 7.34 Hz, 1H), 7.01 – 7.16 (m, 3H), 7.20 – 7.28 (m, 2H), 7.60 (d, J = 7.34 Hz, 1H), 7.73 – 7.81 (m, 2H), 7.86 – 7.99 (m, 2H), 10.20 (br.s, 1H), 12.00 (br s, 1H), 12.25 (s, 1H); 13C NMR (101 MHz, DMSO-d6) delta ppm 14.22, 101.22, 105.88, 120.57, 121.12, 124.49, 128.44, 129.60, 134.23, 138.24, 138.31, 142.32, 158.91, 160.38, 163.83, 174.65. HRMS m/z calculated for C20H18N5O3S2 [M + H+]: 440.0851, found 440.0856.

The synthetic route of 127-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Xinrong; Suarez, Dominic P.; Li, William Hoi Hong; McSherry, Allison K.; Sanchez, Robert M.; Moore, Michael L.; Axten, Jeffrey M.; Tetrahedron Letters; vol. 60; 49; (2019);,
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Application of 6292-59-7, A common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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.

EXAMPLE 20 By reacting 4,6-dichloro-5-[(2-methoxy-4-methyl)phenoxy]pyrimidine with p-t-butylbenzenesulfonamide and thereafter with ethylene glycol Na there was obtained p-t-butyl-N-[6-(2-hydroxyethoxy)-5-[(2-methoxy-p-tolyl)oxy]-4-pyrimidinyl]benzenesulfonamide as a solid.

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US5292740; (1994); A;,
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. 15441-10-8, name is 3-(Aminosulfonyl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H7NO4S

3-sulfamoylpropionic acid (Compound 1) (15.0 g, 97.94 mmol) and 2,4-dihydroxybenzoic acid (Compound 2)(10.2 g, 66.18 mmol) were dissolved in acetic anhydride (22.6 mL). Triethylamine (13.2 mL) was carefully addedto the mixture, andthe mixture was heated for 4 hr.After the reaction, it was cooled and diluted with water.The precipitated product was filtered and washed with aqueous methanol togive (7-hydroxy-2-oxo-2H-chromen-3-yl)methanesulfonamide (Compound 3), 21.2 g, yield 85%.

According to the analysis of related databases, 15441-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeng Qingqiang; (12 pag.)CN108586445; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 4141-08-6, The chemical industry reduces the impact on the environment during synthesis 4141-08-6, name is 2-Amino-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

To a suspension of A-2 (50 mg, 0.19 mmol) in 3 ml AcOEt (3 ml) at rt under an argon atmosphere were added 2-amino-N-methylbenzamide (29 mg, 0.19 mmol) and N-ethyl-diisopropylamine (0.1 ml, 0.59 mmol). The yellow suspension was cooled to 0 C. and propyl-phosphonic anhydride (50% in AcOEt, 0.31 ml, 0.48 mmol) was added. The suspension was stirred at 0 for 30 min and at rt overnight. The solvent was evaporated. The crude product was purified by silica gel chromatography using a CH2Cl2/MeOH gradient to provide the title compound (46 mg, 61%) as yellow solid.MS: M=389.2 (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, 2-Amino-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bleicher, Konrad; Flohr, Alexander; Groebke Zbinden, Katrin; Gruber, Felix; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Sarmiento, Rosa Maria Rodriguez; US2011/306589; (2011); A1;,
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Electric Literature of 120157-98-4,Some common heterocyclic compound, 120157-98-4, name is tert-Butyl acetylcarbamate, molecular formula is C7H13NO3, 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.

Carbonic acid (1 S,4f?)-4-(6-chloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (1 equivalent), acetyl-carbamic acid terf-butyl ester (seeTanaka et al. (1988), supra; 1 .15 equivalents) and triphenyl phosphine (0.15 equivalents) were combined in an oven – dried flask under an atmosphere of argon. Dry deoxygenated THF (to 0.3 M with respect to carbonic acid (1 S,4f?)-4-(6-chloroiDurin-9-yl)-cyclopent-2-enyl ester ethyl ester) was added, followed by Pd2(dba)3 (5 mol%). The reaction mixture was stirred at 500C for 1 hour, and allowed to cool to room temperature, before the volatile components were removed under reduced pressure and the product purified by flash column chromatography/crystallization.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/147659; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 437998-34-0, These common heterocyclic compound, 437998-34-0, name is 2-Amino-3-bromobenzamide, 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 B: Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate from Example 2 Step B (0.49 g, 2.3 mmol) and 2-amino-3-bromobenzamide (0.42 g, 1.9 mmol) were combined in trimethylsilylpolyphosphate (4.3 mL) at rt and the mixture was heated at 115 C. for 20 h with vigorous stirring. The mixture was allowed to cool to rt and then was partitioned between water (15 mL) and ethyl acetate (15 mL). The organic layer was separated and the aqueous layer (pH1) was extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with a 1:10 to 1:1 EtOAc/hexanes to afford 2-[difluoro-(5-fluoro-pyridin-2-yl)-methyl]-8-bromo-3H-quinazolin-4-one as an off-white solid (0.19 g, 22%).

The synthetic route of 437998-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012/53174; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C11H21NO3

To a solution of tert-butyl N-(4- hydroxycyclohexyl)carbamate (710 mg, 3.30 mmol, 1.10 equiv) in 10 mL of distilled THF was added sodium hydride (60% dispersion in mineral oil, 720 mg, 18.00 mmol, 6.00 equiv) at room temperature under nitrogen. After stirring for 30 min, intermediate 15.4 (891 mg, 3.00 mmol, 1.00 equiv) in THF (10 mL) was added via syringe and the resulting solution was stirred for 12 h at room temperature. The reaction was then quenched by the addition of water and extracted with 3 x 50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1 :4 to 1 :2). Purification afforded 18.1 (260 mg, 18%) as a white solid.

The synthetic route of 111300-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine, C.; WESTER, Ronald T.; ROMERO, Donna L.; ROBINSON, Shaughnessy; SHELLEY, Mee; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; MASSE, Craig E.; KAPELLER-LIBERMANN, Rosana; WO2013/106535; (2013); A1;,
Amide – Wikipedia,
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Related Products of 1314538-55-0, 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. 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Boc20 (178 uL, 0.77 mmol) was added to a solution of (4-(aminomethyl)phenyl)boronic acid hydrochloride (143 mg, 0.77 mmol) and Cs2C03 (665 mg, 2.04 mmol) in DME (10 mL) and water (1.0 mL) at rt. After being stirred at rt for 30 min, Suzuki coupling was carried out as follow: 2-chloro-N-(3- (lH-imidazol-l-yl)propyl)-3-phenylquinoxaline-6-carboxamide (201 mg, 0.54 mmol) (prepared according to Example 3, step 7) and Pd(dppf)Cl2? CH2C12 (42.0 mg, 51.4 muiotaetaomicron) were added to the reaction mixture. The mixture was heated at 100 C for 10 h under microwave irradiation. After cooling, the mixture was poured into saturated aqueous solution of NaHC03 and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04 and concentrated in vacuo. The residue was purified by NH silica gel chromatography to give teri-butyl [4-(6-{[3-(lH-imidazol-l- yl)propyl]carbamoyl}-3-phenylquinoxalin-2-yl)benzyl]carbamate (187 mg, 65%, H NMR (300 MHz, DMSO-i/6) delta 1.23-1.52 (m, 9 H), 2.00-2.12 (m, 2 H), 3.32-3.39 (m, 2 H), 4.05^1.19 (m, 4 H), 6.91 (s, 1 H), 7.10-7.30 (m, 3 H), 7.32-7.77 (m, 9 H), 8.12-8.38 (m, 2 H), 8.69 (d, J= 1.3 Hz, 1 H), 8.91 (t, J= 5.2 Hz, 1 H)

The chemical industry reduces the impact on the environment during synthesis Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; GIGSTAD, Kenneth, M.; CARDIN, David, P.; HIRAYAMA, Takaharu; HIROSE, Masaaki; HU, Yongbo; KAKEI, Hiroyuki; LEE, Hong, Myung; MOTOYAJI, Takashi; NII, Noriyuki; SHI, Zhan; VYSKOCIL, Stepan; WATANABE, Hiroyuki; WO2015/161142; (2015); A1;,
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Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 598-55-0, name is Methyl carbamate, 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 598-55-0, category: amides-buliding-blocks

To a solution of methyl carbamate (20.0 g, 266 mmol) in diethyl ether (300 ml) was added SOCl2 (21.0 mL, 288 mmol) at 0 C, after stirring for 5 min the reaction mixture was allowed to warm to rt and stirred for a further 30 min. A solution of pyridine (40.9 mL, 506 mmol) in diethyl ether (60.0 mL) was added slowly over 1.5 h and then stirred for further 1.5 h. The resulting precipitate was filtered under N2. The filtrate was concentrated in vacuo to give 9 (32.0 g, 264 mmol, Quant.) as yellow oil. The material was used without any further purification [1H NMR (400 MHz, CDCl3) delta 3.94 (3H, s, CH3)]. To a solution of methyl N-(sulfinylidene)carbamate (9, 10.0 g, 83 mmol) in benzene (60.0 mL) was added freshly distilled cyclopentadiene (9.7 mL, 116 mmol) dropwise and the resulting solution was stirred for 20 h at rt. The solution was diluted with THF (110 mL) and phenylmagnesium bromide (1 M in THF, 83.0 mL, 83 mmol) was added over 45 min then stirred for 30 min before being quenched by addition of satd aq NH4Cl (100 mL). Extracted with EtOAc (3 × 100 mL), combined organic phases were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo. Purification (MPLC, Si, EtOAc/petrol, 80%) gave 10 as mixture of diastereomers in approx. 85% purity, which was used in the subsequent reaction (10.4 g, thick oil, estimated 48% yield taking into account small impurities). 4.2.1 Compound 1012b Orange coloured oil. Rf = 0.72 (EtOAc); IR cm-1 3011, 2360, 2341, 1716, 1516; 1H NMR (400 MHz, CDCl3) delta 7.57-7.47 (5H, m, H-Ar), 6.17-5.99 (2H, m, H-2 and H-3), 5.83 (1H, d, J = 8.8 Hz, NH), 4.78 (1H, dd, J = 8.8 and 8.7 Hz, H-1), 3.84-3.78 (1H, m, H-4), 3.68 (3H, s, CH3), 2.17 (1H, ddd, J = 15.3, 8.7 and 8.5 Hz, H-5), 1.78-1.73 (1H, m, H-5); 13C NMR (100 MHz, CDCl3) 171.1 (CO2Me), 156.3 (C-Ar), 142.0 (C-2 or C-3), 130.9 (C-Ar), 129.3 (C-Ar), 129.1 (C-Ar), 128.0 (C-2 or C-3), 124.0 (C-Ar), 71.2 (C-4), 53.4 (C-1), 52.0 (CH3), 29.2 (C-5); HRMS ESI+ m/z C13H15NO3S calculated: 288.0665 [M+Na]+, found: 288.0654

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:
Article; Cully, Sarah J.; Storr, Thomas E.; Rawling, Michael J.; Abeysena, Induka R.; Hamza, Daniel; Jones, Geraint; Pearce, Christopher A.; Quddus, Abdul; Lewis, William; Stockman, Robert A.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5249 – 5257;,
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 640-61-9 as follows. HPLC of Formula: C8H11NO2S

Add 0.2 mmol of N-methyl-p-toluenesulfonamide and a stirrer to a clean Schlenk reaction tube.Then, 1.0 mL of DMF solvent was added by syringe, and 1.0 mmol of NaOH was added to the reaction tube.Finally, 0.6 mmol of 1,1-dichloroethylene was added with a micro syringe, and the bottle was stoppered with a soft rubber stopper, and reacted at 70 C for 24 hours.TLC dot plate detection; after the reaction is completed, the reaction solution is added with ice water and extracted with ethyl acetate three times.The organic layer is concentrated and separated by column chromatography to obtain pure N-methyl-N-ethynyl p-toluenesulfonamide.White solid, yield 93%.

According to the analysis of related databases, 640-61-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangxi Normal University; Zhao Junfeng; Tu Yongliang; Zeng Xianzhu; (9 pag.)CN109320441; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics