Month: March 2021

711007-44-2, name is 2,3-Diaminobenzamide, 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 2,3-Diaminobenzamide

A mixture of 2,3-diamino-benzamide (1,51 g, 10.0 mmoles) or a 2, 3-DIAMINO- (N-SUBSTITUTED)-BENZAMIDE (10.0 mmoles) and a suitable paramagnetic aldehyde (of general formula V) or dia- magnetic aldehyde (of general formula VI) (10.0 mol), and toluene-p-sulphonic acid monohydrate (95 mg, 0.5 mmoles) is refluxed in toluene (40 mL) or in an other appropriate solvent till all the starting compounds are consumed (4-6 hours) under Dean and Stark apparatus. Then the solvent is evaporated in vacuo, the residue dissolved in CHC13 (50 mL) or in some other halogenated solvent, and an appropriate oxidant such as acti- vated Mn02 (4.30 g, 50.0 mmoles) is added and the mixture is stirred and refluxed for about 6 hours. The mixture was fil- tered through Cellite, evaporated and the residue was purified by flash column chromatography (CHCl3/Et2O or CHC13/MEOH) or crystallization to give compound la or Ib (yield: 39-73 %)

The synthetic route of 711007-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HIDEG, Kalman; KALAI, Tamas; SUeMEGI, Balazs; WO2004/96793; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

4141-08-6, name is 2-Amino-N-methylbenzamide, 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. Computed Properties of C8H10N2O

Step 2: Preparation of 2-((2,5-dichloropyrimidin-4-yl)amino)-N-methylbenzamide (3); 2-Arrdno-N-iTiethylbenzarnide (2, 9 g, 60 mmol) and potassium carbonate ( 16.5 g, 120 mmol) were taken up in dimethylformamide (DMF )( 100 mL) to form a mixture and the mixture was stirred for 10 min. 2,4,5-trichloropyrimidine ( 1 1 g, 60 mmol) was added drop wise to the mixture and the mixture was stirred at 80 C for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled and filtered through a Buckner funnel. The filtered solid was washed with water and dried to afford 2-((2,5-dichloropyrimidin-4-yl)amino)-N-methylbenzamide as a light yellow solid (3, 15.2 g, 85.8%). NMR (DMSO-i/6): delta 8.90 (bs, 1 H), 8.60-8.40 (m, 1 H), 7.80-7.60 (d, 1 H), 7.70-7.50 (t, 1 H), 7.30-7.20 (t, 1 H), 2.80 (s, 3H).

The synthetic route of 4141-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GATEKEEPER PHARMACEUTICALS, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun; WO2011/140338; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 37045-73-1, These common heterocyclic compound, 37045-73-1, name is 3-(Methylsulfonamido)aniline, 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.

Intermediate 6 (41 mg, 0.121 mmol), N-(3-amino-phenyl)-methane sulfonamide (68 mg, 0.365 mmol), glacial acetic acid (8 mul, 0.121 mmol) and n-butanol (1.3 ml) were combined and irradiated at 150 0C for 40 minutes in a Biotage 1-60 microwave reactor. The reaction mixture was evaporated and then purified by preparative LCMS (low pH buffer) to give a white solid (42 mg, 57%). 1H nuMR (400 MHz, DMSO-Cf6) delta ppm 0.53 – 0.61 (m, 2 H), 0.86 – 0.93 (m, 2 H), 1.49 – 1.57 (m, 1 H), 1.80 – 1.89 (m, 2 H), 3.00 (s, 3 H), 3.27 – 3.35 (m, 2 H), 3.53 – 3.61 (m, 2 H), 6.92 – 6.97 (m, 1 H), 7.13 (dd, 7=4.8, 3.9 Hz, 1 H), 7.27 – 7.34 (m, 1 H), 7.36 – 7.42 (m, 2 H), 7.58 (s, 1 H), 7.68 – 7.76 (m, 2 H), 8.46 – 8.60 (m, 2 H), 9.86 (s, 1 H), 10.20 (br. s, 1 H); m/z (ES+APCI)+: 487 [M+H]+.

The synthetic route of 37045-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL; WO2009/122180; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 177906-48-8, A common heterocyclic compound, 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, molecular formula is C11H22N2O2, 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.

To a solution of tert-butyl ((lr,4r)-4-aminocyclohexyl)carbamate (1 g, 4.66 mmol) and 1 -fluoro-2-nitrobenzene (commercially available from Sigma- Aldrich, Milwaukee, WI) (0.658 g, 4.66 mmol) in DMF (5 mL) was added K2C03 (1.28 g, 9.32 mmol) at ambient temperature. The resulting reaction mixture was stirred for 12 hours at 60C. After completion of reaction (monitored by TLC (TLC eluent: 30 % EtOAc in petroleum ether)), the reaction mixture was cooled to ambient temperature and water was added to obtain a yellow precipitate. After stirring for 10 minutes, the mixture was filtered and washed with water and then dried under vacuum to afford tert-butyl ((lr,4r)-4-((2-nitrophenyl)amino)cyclohexyl)carbamate as a yellow solid (1.5 g, 95.84 %). lB NMR (300 MHz, DMSO-d6) delta 8.03 (d, J= 8.6 Hz, 1H), 7.87 (d, J= 7.6 Hz, 1H), 7.52-7.43 (m, 1H), 7.1 1 (d, J= 8.7 Hz, 1H), 6.83 (d, J= 7.6 Hz, 1H), 6.71 – 6.57 (m, 1H), 3.42 (m, 1H), 1.99 (s, 2H), 1.81 (s, 2H), 1.45 – 1.20 (m, 2H+2H+1H+9H=14H). m/z (ESI) 336.3 (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; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); 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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1,1-Trifluoro-N-phenylmethanesulfonamide

To a solution in 2-[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester, 18, (0.312 g, 1.23 mmol) in MeOH (10 mL) containing diisopropylethylamine (0.214 mL, 1.23 mmol) at 0 C. under N2 is added N-phenyltrifluoromethanesulfonamide (0.439 g, 1.23 mmol). The reaction is warmed slowly to room temperature and stirred for 40 hours. The solvent is removed under reduced pressure and the crude oil which remains is purified over silica (EtOAc:heptane 1:9) to afford 0.170 g (36% yield) of the desired compound as a yellow oil. 1H NMR (250 MHz, MeOD) delta ppm 8.85 (1H, br s), 8.19 (1H, d, J=2.4 Hz), 7.46 (1 H, d, J=2.3 Hz), 3.74 (3H, s), 1.63 (6H , s). HPLC-MS: m/z 387 [M+H]+.

According to the analysis of related databases, 456-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Procter & Gamble Company; US2007/299086; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 28797-48-0, name is 11-(2-Chloroacetyl)-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-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 28797-48-0, Formula: C14H10ClN3O2

EXAMPLE 13 5,11-Dihydro-11-[[4-(1-methyl-4-piperidinyl)-1-piperidinyl]acetyl]- 6H-pyrido[2,3-b][1,4]benzodiazepin-6-one Prepared analogously to Example 1 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 4-(1-methyl-4-piperidinyl)piperidine in a yield of 23% of theory. Colourless crystals, m.p. 208-211 C. (ethyl acetate).

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; Dr. Karl Thomae, GmbH; US5175158; (1992); A;,
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 193751-54-1 as follows. Safety of tert-Butyl cyclopent-3-en-1-ylcarbamate

To a stirred suspension of LiAlH4 (3.74 g, 0.09852 mol) in 200 ml anhydrous THF in a two neck RBF (IL), was added a solution of 514 (10 g, 0.04926 mol) in 70 mL of THF slowly at 0 C under nitrogen atmosphere. After complete addition, reaction mixture was warmed to room temperature and then heated to reflux for 4 h. Progress of the reaction was monitored by TLC. After completion of reaction (by TLC) the mixture was cooled to 0 C and quenched with careful addition of saturated Na2SO4 solution. Reaction mixture was stirred for 4 h at room temperature and filtered off. Residue was washed well with THF. The filtrate and washings were mixed and diluted with 400 mL dioxane and 26 mL conc. HCl and stirred for 20 minutes at room temperature. The volatilities were stripped off under vacuum to furnish the hydrochloride salt of 515 as a white solid. Yield: 7.12 g 1H-NMR (DMSO, 400 MHz): delta=9.34 (broad, 2H), 5.68 (s, 2H), 3.74 (m, 1H), 2.66-2.60 (m, 2H), 2.50-2.45 (m, 5H).

According to the analysis of related databases, 193751-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alnylam Pharmaceuticals, Inc.; Fitzgerald, Kevin; Butler, James; Bettencourt, Brian; Borodovsky, Anna; Kuchimanchi, Satyanarayana; Charisse, Klaus; Manoharan, Muthiah; Maier, Martin; Rajeev, Kallanthottathil G.; Foster, Donald; US2015/247143; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 15441-10-8, name is 3-(Aminosulfonyl)propanoic acid, 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. name: 3-(Aminosulfonyl)propanoic acid

General procedure: To a solution of 3-(4-((2-aminopropyl)thio)-1 ,2,5-oxadiazol-3-yl)-4-(3-(difluoromethyl)-4- fluorophenyl)-1 ,2,4-oxadiazol-5(4H)-one hydroiodide (Int 102) (416 mg, 0.81 mmol), HATU (462 mg, 1 .22 mmol) and Et3N (245 mg, 2.43 mmol) in DMF (8 mL) 2- sulfamoylacetic acid (135 mg, 0.97 mmol) was added and the mixture was stirred at rt overnight. EtOAc (20 mL) was added and the mixture was extracted with water (2 x 20 mL). The combined organic layers were dried over anhydrous Na2S0 , filtered and concentrated to dryness. The residue was purified by column chromatography to give the title compound as a white solid.

The synthetic route of 3-(Aminosulfonyl)propanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX DISCOVERY VERWALTUNGS-GMBH; STEENECK, Christoph; KINZEL, Olaf; ANDERHUB, Simon; HORNBERGER, Martin; KLEYMANN, Gerald; HOFFMANN, Thomas; (191 pag.)WO2018/83241; (2018); 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 35303-76-5 as follows. COA of Formula: C8H12N2O2S

Step 4. (S)-tert-butyl 6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoate A solution of (S)-4-(3-((S)-6-(bis((1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-1-tert-butoxy-1-oxohexan-2-yl)ureido)-5-tert-butoxy-5-oxopentanoic acid (80 mg, 0.098 mmol), 4-(2-aminoethyl)benzenesulfonamide (30 mg, 0.15 mmol), 2-(1-H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU, 50 mg, 0.17 mmol), and DIPEA (0.50 mL) in DMF (5 mL) was stirred at 40 ¡ãC overnight. The solvents were evaporated under reduced pressure to give a residue, which was purified by Biotage SP4 using a gradient of 0-20percent MeOH in DCM to give (S)-tert-butyl 6-(bis((1-(2-tet¡ãt-butoxy-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)-2-(3-((S)-1-tert-butoxy-1,5-dioxo-5-(4-sulfamoylphenethylamino)pentan-2-yl)ureido)hexanoate (100 mg, 100percent). ESMS m/z: 501.9 (M/2+H)+.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Molecular Insight Pharmaceuticals, Inc.; Babich, John W.; Zimmerman, Craig N.; Joyal, John; Maresca, Kevin P.; Marquis, John; Lu, Genliang; Wang, Jian-cheng; Hillier, Shawn; (110 pag.)EP2706057; (2016); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 121-30-2, 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 121-30-2 as follows.

To the product of Example 74a (1.63 g, 10 mmol) and 2-amino-6-chloro-1,3-benzenedisulfonamide (Aldrich Chemical Co.,1.439 g, 5 mmol) in anhydrous dioxane (50 mL) was added Amberlyst (15) wet strongly acidic resin (3 g). The reaction mixture was stirred gently at room temperature for 2 days, then decanted into another flask. The resin was washed with dioxane (2 mL) and the washings added to the reaction mixture. Fresh Amberlyst (15) wet strongly acidic resin (2 g) was added to the reaction mixture and the stirring was continued at room temperature for 24 hours. The resin was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was treated with ethyl acetate and washed with saturated aqueous sodium carbonate, water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by column chromatography over silica gel, eluting with 3% methanol in dichloromethane gave 1.3 g of an oil that was triturated with 20% ethyl acetate in hexane to give the title compound (1.1 g, 54% yield) as a white solid: mp 113-117 C.; 1H NMR (d6-DMSO) delta 8.03 (s, 1H), 8.01 (s, 1H), 7.97 (s, 1H), 7.52 (s, 2H), 6.98 (s, 1H), 4.96-4.89 (m, 1H), 4.77-4.65 (m, 2H), 2.28-2.15 (m, 2H); 13C NMR (d6-DMSO) delta 146.3, 134.2, 128.6, 125.4, 118.2, 117.1, 69.1, 63.3, 30.4. Mass spectrum (API-TIS) m/z 404 (MH)+, 406 (MH+2)+.

According to the analysis of related databases, 121-30-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics