Month: August 2021

Synthetic Route of 550-89-0, These common heterocyclic compound, 550-89-0, name is Phenazine-1-carboxamide, 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 1: Synthesis of 1-amino-phenazineA solution of sodium methanolate (25% in MeOH, 24.6 ml, 107 mmol) in 100 ml MeOH was cooled to -78C and a solution of bromine (2.10 ml, 40.9 mmol) in 10.0 ml MeOH was added over a period of 2 min. Under further cooling the solution was first stirred 5 min followed by the addition of phenazine- 1-carboxamide (4.00 g, 17.9 mmol) in 200 ml dry methanol and 400 ml dry THF over a period of 1 h via dropping funnel. After the complete addition a clear orange solution was obtained that was warmed to room temperature and further stirred 2 h at 55C. Following the mixture was cooled down to room temperature and stirred further 72 h. After evaporating under reduced pressure the residue was dissolved in methanol (300 ml) and aqueous NaOH (40%, 150 ml) and refluxed for 4 h at 90C. Subsequently the solution was cooled down to 0C and set to pH 8.5 with concentrated HC1, obtain- ing a dark red suspension. After concentrating to about 200 ml under reduced pressure 500 ml water was added. The mixture was extracted three times with CHC13. The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (n-hexane/ethyl acetate, 80:20 -> 75:25) obtaining 2.86 g (82%) of the title compound as dark red solid.

The synthetic route of 550-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROCHE DIAGNOSTICS GMBH; F. HOFFMANN-LA ROCHE AG; ROCHE DIAGNOSTICS OPERATIONS, INC.; HEINDL, Dieter; NORTMEYER, Christine; GEBAUER, Peter; HUNT DU VALL, Stacy; BAUER-ESPINDOLA, Klaus Andreas; WO2015/158645; (2015); A1;,
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Some common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, 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: tert-Butyl 3-aminobenzylcarbamate

a) fert-Butyl 3-((7-chloro-5-hydroxy-1 ,1 -dioxido-2H-benzo[e][1 ,2,4]thiadiazin-3- yl)amino)benzylcarbamate (3107) To a stirred solution of 3-bromo-7-chloro-5-hydroxy-2H-benzo[e][1 ,2,4]thiadiazine 1 ,1 – dioxide (lnt-3, 400 mg) in fe/f-butanol (15 mL) at room temperature in a sealed tube were added fe/ -butyl 3-aminobenzylcarbamate (342 mg) and potassium dihydrogenphosphate (210 mg). The reaction mixture was warmed to 100 C for 16 h. The reaction mixture was cooled to room temperature and diluted with cold water. The solids were collected by filtration and dried under reduced pressure. The solids were triturated with diethyl ether and pentane to afford titled compound (250 mg) as an off-white solid. LCMS 396.98 m/z (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 147291-66-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
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Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 116091-63-5, name is 2-Methoxy-5-(2-oxopropyl)benzenesulfonamide, 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 116091-63-5, Safety of 2-Methoxy-5-(2-oxopropyl)benzenesulfonamide

1.2. Hydrogenation on platinum according to EP 0 257 787 (1987); III yield 53% V The catalyst is used in the amount of 1 g/1 mol of ketone, hydrogenation takes place in methanol under normal pressure for 20 hours. For purification to the desired optical purity (below 0.2 %), the substance is purified 4x in acetone and 3x in a mixture of water and acetone.

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; ZENTIVA, A.S.; WO2005/75415; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 154350-29-5, These common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, 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.

A solution of compound 1-1 (0.52 g, 2.3 mmol), 2-(lH-7-azabenzotriazol-l-yl)- 1,1 ,3,3-tetramethyl uronium hexafluoro -phosphate methanaminium (HATU, 1.74 g, 4.6 mmol), and 4-dimethylaminopyridine (1.39 g, 1 1.6 mmol) in CH2CI2 (40 mL) was stirred at room temperature for 1 hour, followed by slow addition ofcyclopropanesulfonamide (0.57 g, 4.7 mmol), diisopropylethylamine (1.81 mL, 14.0 mmol), and l ,8-diazabicyclo[5,4,0]undec-7-ene (1.80 g, 11.7 mmol) over15 minutes. After the reaction mixture was stirred at room temperature overnight, the solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give compound 1-2 (0.51 g, 66percent). MS m/z 353.1 (M++23); !H NMR (CDCI3) d 9.75 (brs, 1H), 5.64-5.51 (m, 1H), 5.30 (d, J = 17.4 H), 5.16 (d, J = 10.2 Hz, 1H), 2.95-2.89 (m, 1H), 2.19-2.10 (m, 1H), 1.93-1.88 (m, 1H), 1.47 (s, 9H), 1.46-1.38 (m, 1H), 1.32-1.23 (m, 2H), 1.15-1.00 (m, 2H).

The synthetic route of 154350-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIGEN BIOTECHNOLOGY CO., LTD.; LIU, Chen-Fu; LEE, Kuang-Yuan; CHENG, Pei-Chin; LIU, Yo-Chin; LO, Pin; TSENG, Kuo-Feng; CHEN, Chih-Ming; KING, Chi-Hsin Richard; LIN, Chu-Chung; WO2011/34518; (2011); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 19982-07-1, name is N-(3,5-Dimethyladamantan-1-yl)acetamide, 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 19982-07-1, name: N-(3,5-Dimethyladamantan-1-yl)acetamide

[0063] 1.00 g (5.50 mmol) of 3,5-dimethyl-1-adamantanol, 0.46 g (11.1 mmol) of acetonitrile, and 9.61 g of mesitylenewere added to a test tube having an outer diameter of 30 mm to obtain a mixed solution. Then, 1.12 g (11.1 mmol) of97% concentrated sulfuric acid was dropped into the mixed solution in the test tube to obtain a reaction solution. Theobtained reaction solution was stirred at 30C for 3 hours to continue the reaction. Then, 6.09 g of water was added tothe reaction solution to stop the reaction, and an aqueous phase was removed by washing from the reaction solution toobtain a mesitylene solution containing 1-acetamido-3,5-dimethyladamantane (reaction yield: 80.4%). Then, 0.71 g ofsodium hydrate (NaOH) and 9.61 g of 1-hexanol were added to the obtained solution to obtain a reaction solution. The obtained reaction solution was stirred at 130C for 18 hours to hydrolyze 1-acetamido-3,5-dimethyladamantane. Then,in the reaction solution, the generation of memantine was confirmed by GC (reaction yield: 96.2%).

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; Mitsubishi Gas Chemical Company, Inc.; SHIMO, Tetsuya; EP2949643; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 112257-19-9, These common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

tert-Butyl N-methyl-N-(2-methylaminoethyl)carbamate (Intermediate 173, 300 mg, 1.59 mmol) was added to a suspension of N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-indol-3-yl)pyrimidin-2-amine (Intermediate 129, 522 mg, 1.33 mmol) and DIPEA (0.462 mL, 2.65 mmol) in DMA (5 mL). The mixture was heated in a microwave at 100C for 4h. The mixture was then diluted with EtOAc and washed with water (5x), brine, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-2% CH3OH in CH2Cl2 gave the title compound (431 mg, 58%) as an orange solid after trituration with diethyl ether; 1H NMR: 1.37 (9H, s), 2.79 (3H, s), 2.88 (3H, s), 3.29-3.36 (2H, m), 3.39-3.44 (2H, m), 3.89 (3H, s), 3.99 (3H, s), 6.85 (1H, d), 7.14 (1H, t), 7.21-7.28 (2H, m), 7.53 (1H, br d), 8.04 (1H, s), 8.31-8.38 (3H, m), 8.72 (1H, br s); m/z: ES+ MH+ 562.35.

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; FINLAY, Maurice, Raymond, Verschoyle; WARD, Richard, Andrew; KADAMBAR, Vasantha, Krishna; CHANDRASHEKAR, Reddy, C.; MURUGAN, Andiappan; REDFEARN, Heather, Marie; WO2013/14448; (2013); A1;,
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Electric Literature of 90-16-4, A common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, molecular formula is C7H5N3O, 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: Intermediates 3a-h were prepared by the similar method described in the literature [2] (Scheme 1). A stirring mixture of 2 (8 mmol), 1,3-dibromopropane (4.1 mL, 40 mmol) and potassium carbonate (2.208 g, 16 mmol) in acetone (200 mL) was heated to reflux and monitored by TLC. After the complete consumption of 2, the solvent was removed under reduced pressure. Then the residue was taken up in water and extracted with CH2Cl2 (80 mL ×3). The combined organic layer wasdried over anhydrous Na2SO4, concentrated and purified by flash column chromatography on silica gel using petroleum ether (60-90 C)/EtOAc (4:1) as eluent to yield 3. Intermediates 4a-h were prepared by the same method as above, using 1,4-dibromobutane instead of 1,3-dibromopropane.

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; Wang, Gao-Lei; Chen, Xi; Chang, Ya-Ning; Du, Dan; Li, Zhong; Xu, Xiao-Yong; Chinese Chemical Letters; vol. 26; 12; (2015); p. 1502 – 1506;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, 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 147356-78-3, category: amides-buliding-blocks

To a solution of (5S,7S)-2-bromo-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[l,2- b][l,2,4]triazole (150 mg, 0.47 mmol), N-methoxy-N-methyl-cyclopropanecarboxamide (122 mg, 0.94 mmol) in tetrahydrofuran (3 mL) was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 0.47 mL, 0.94mmol) dropwise at 0 C. After addition, the mixture was stirred at 0 C for 0.5 h and quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by RP-HPLC (acetonitrile 40-70%o / 0.225%o formic acid in water) to afford arbitrarily assigned cyclopropyl-[(5S,7S)-5-(2,3-difluorophenyl)-7-fluoro-6,7-dihydro-5H- pyrrolo[l,2-b] [l,2,4]triazol-2-yl]methanone (49.1 mg, 34%) as a white solid. lR NMR (400 MHz, CDCl3) delta 7.22 – 7.16 (m, 1H), 7.14 – 7.08 (m, 1H), 6.75 – 6.72 (m, 1H), 6.13 – 6.10 (m, 0.5H), 5.99 – 5.96 (m, 0.5H), 5.88 – 5.84 (m, 1H), 3.74 – 3.67 (m, 1H), 3.09 – 3.04 (m, 1H), 2.99 – 2.92 (m, 1H), 1.36 – 1.31 (m, 2H), 1.14 – 1.09 (m, 2H). LC-MS RT = 0.666 min, m/z = 308.1 [M+H]+. LCMS (5 to 95%o acetonitrile in water + 0.03 %> trifluoacetic acid over 1.5 mins) retention time 0.666 min, ESI+ found [M+H] = 308.1.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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. 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 579474-47-8

Example M5 {4-Fluoro-2-[3-oxo-3-(3-pyridin-4-yl-phenyl)-propionylamino]-phenyl}-carbamic acid tert-butyl ester The title compound was prepared from (2-amino-4-fluoro-phenyl)-carbamic acid tert-butyl ester (Example J2) (170 mg, 0.75 mmol) and 3-oxo-3-(3-pyridin-4-yl-phenyl)-propionic acid tert-butyl ester (Example K2) (223 mg, 0.75 mmol) according to the general procedure M. Obtained as an off-white solid (251 mg). MS (ISP) 450.4 [(M+H)+]; mp 110-115 C.

The synthetic route of 579474-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adam, Geo; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2003/166639; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108-13-4, name is Malonamide, 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. name: Malonamide

B-1. 1,2-Dihydro-5-(4-methoxyphenyl)-2-oxonicotinamide–A mixture containing 82.1 g. of 3-dimethylamino-2-(4-methoxyphenyl)-2-propenal, 63.15 g. of malonamide (97%), 54.0 g. of sodium methoxide and 800 ml. of methanol was refluxed with stirring for about 17 hours and chilled. The reaction mixture was filtered and the filtrate concentrated in vacuo to a volume of about 500 ml., acidified with acetic acid and chilled. The resulting solid was collected, dried at 90 C. in a vacuum oven to yield 25.25 g. of 1,2-dihydro-5-(4-methoxyphenyl)-2-oxonicotinamide, m.p. 283-286 C.

The synthetic route of 108-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sterling Drug Inc.; US4515797; (1985); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics