Category: amides-buliding-blocks

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,
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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

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

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

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

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

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

Reference of 673-66-5, 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. 673-66-5, name is Azocan-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Dimethyl sulfate (1.42 mL, 15 mmol) and 2-azacyclooctanone (1.91 g, 15 mmol) were added to a dried, argon flushed 2-necked round bottomed flask and the mixture was heated at 60 0C for 23 h. The mixture was then cooled to r.t. and added to a saturated aq. solution of Na2CO3 (100 mL). This solution was extracted with ether, dried over Na2SO4, filtrated and evaporated to give a brownish oil of the title compound (1.71 g, 81%). 1H NMR (CDCl3) delta: 3.62 (s, 3H); 3.44-3.40 (m, 2H); 2.34-2.30 (m, 2H); 1-71-1.65 (m, 2H); 1.64-1.58 (m, 2H); 1.50-1.44 (m, 2H); 1.42-1.35 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis Azocan-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; WO2008/64136; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 16982-21-1

4-Chloromethyl-thiazole-2-carboxylic acid ethyl ester was prepared according to Summers, J. B., Jr. et al. (U.S. Pat. No. 5,486,525): A mixture of ethyl thiooxamate (7.0 g, 52.6 mmol) and 1,3-dichloroacetone (7.0 g, 55.1 mmol) in ethanol (300 mL) was heated at reflux overnight. The solvent was evaporated under reduced pressure, and the crude material was partitioned between methylene chloride and aqueous sodium hydrogen carbonate. The organic layer was dried (magnesium sulfate), filtered, evaporated and purified by chromatography on flash silica gel, eluting with 15% ethyl acetate/hexane to give 4-chloromethyl-thiazole-2-carboxylic acid ethyl ester (4.0 g, 37%) as an orange oil. 1HNMR (CDCl3): 6 7.64 (s, 1H), 4.78 (s, 2H), 4.51 (q, J=7.0 Hz, 2H), 1.46 (t, J=7.0 Hz, 3H). MS (APCI+): 206 (100).

The synthetic route of 16982-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 144222-23-1, 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. 144222-23-1, name is tert-Butyl 4-aminobutyl(methyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of l-(4-chloro-6-methyl-2-pyrimidinyl)-3-(3,4-dichlorophenyl)urea (1) (1.4g, 4.3mmol) and toluene (6.5 mL) was heated to reflux with stirring. To this was added N- (4-Aminobutyl)-N-methyl carbamic acid tert-butyl ester (1.0 g, 5.2 mmol), and triethylamine (0.91 mL, 6.4 mmol) and reflux continued for 30 minutes. Upon cooling methanol was added and the precipitate formed was filtered and washed with diethyl ether to give the title compound (25) (2.0 g, 90%). LC/MS: Rt = 3.97 min, m/z = 497.2-499.2 [MH+].

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 4-aminobutyl(methyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CURTANA PHARMACEUTICALS, INC.; BEATON, Graham; TUCCI, Fabio C.; RAVULA, Satheesh B.; MCHARDY, Stanton F.; RUIZ, Francisco Xavier, III; LOPEZ, Ambrosio, Jr.; CAMPOS, Bismarck; WANG, Hua-Yu Leo; (241 pag.)WO2016/138479; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics