Author: Jessica.F

Electric Literature of 758-96-3, 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 758-96-3 as follows.

General procedure: To a solution of 5-chloro-N-cyanothiophene-2-carboximidamide in CH3CN was added N,N-dimethylacetamide and POCl3. The mixture was stirred at 70 C overnight under N2. TLC showed starting material was consumed. The mixture was then poured into NaHCO3 (aq) carefully and the precipitate collected. The dried compound was taken to the next step without further purification.

According to the analysis of related databases, 758-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hagen, Timothy J.; Mo, Xuesheng; Burgin, Alex B.; Fox III, David; Zhang, Zheng; Gurney, Mark E.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 4031 – 4034;,
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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. 16313-66-9, name is 2-Amino-5-bromobenzamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7BrN2O

General procedure: 3.3.1 6-Bromo-8-iodo-2-phenylquinazolin-4(3H)-one (4a) A stirred mixture of 2 (1.00 g, 2.94 mmol), benzaldehyde (0.37 g, 3.52 mmol) and iodine (1.49 g, 5.88 mmol) in ethanol (100 mL) was refluxed for 7 h and then allowed to cool to room temperature. The mixture was quenched with an ice-cold aqueous sodium thiosulfate solution and the precipitate was filtered and recrystallized to afford 4a as a white solid (1.10 g, 87%), mp>345 C; numax (ATR) 527, 552, 636, 688, 698, 848, 946, 1129, 1291, 1384, 1446, 1470, 1563, 1598, 1658, 3073, 3164 cm-1; deltaH (500 MHz, DMSO-d6) 7.56-7.62 (m, 3H), 8.20 (d, J=2.0 Hz, 1H), 8.25-8.29 (m, 2H), 8.49 (d, J=2.0 Hz, 1H), 12.86 (s, 1H); deltaC (125 MHz, DMSO-d6) 103.5, 119.7, 122.9, 128.5, 128.9, 129.2, 132.4, 132.7, 145.9, 148.1, 153.7, 161.7; m/z 427 (100, MH+); HRMS (ES): MH+, found 426.8937. C14H979BrIN2O+ requires 426.8943.

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:
Article; Paumo, Hugues K.; Mphahlele, Malose J.; Rhyman, Lydia; Ramasami, Ponnadurai; Tetrahedron; vol. 72; 1; (2016); p. 123 – 133;,
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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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C10H12BrNO2

A solution of benzyl 2-bromoethylcarbamate (7.23 g), tert-butyl 4-piperidinyl-carbamate formic acid salt (4.63 g) and triethylamine (8 ml) in acetonitrile (30 ml) was heated at reflux for 24 hours. After the reaction mixture was concentrated under reduced pressure, water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane) to obtain benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate (5.5 g) as colorless crystals. 1H-NMR (200 MHz, CDCl3) delta1.22-1.43 (2H, m), 1.44 (9H, s), 1.84-1.97 (2H, m), 2.01-2.16 (2H, m), 2.39-2.49 (2H, m), 2.71-2.85 (2H, m), 3.23-3.35 (2H, m), 3.36-3.54 (1H, m), 4.29-4.54 (1H, m), 5.10 (2H, s), 5.18-5.32 (1H, m), 7.29-7.42 (5H, 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 53844-02-3.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6627651; (2003); B1;,
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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;,
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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. 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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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