Month: August 2021

Synthetic Route of 2227-79-4, These common heterocyclic compound, 2227-79-4, name is Benzothioamide, 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: To a stirred solution of aryl thioamide or amidine (1 mmol) in 5 mL distilled water was added alpha-tosyloxyketone (1 mmol) and the reaction mixture stirred at 60 C or 80 C till completion. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, product was readily filtered and recrystallized from ethanol (3a-k, 3p-o and 4a-e). In some cases (3l-m and 4f-i) product was extracted with dichloromethane (25 mL), washed with brine (25 mL), the organic layers were combined, dried over anhydrous Na2SO4 and distilled off in vacuum. The residue so obtained was purified by column chromatography on silica gel (100-200 mesh) (EtOAc/Hexane) to give pure product.

Statistics shows that Benzothioamide is playing an increasingly important role. we look forward to future research findings about 2227-79-4.

Reference:
Article; Kumar, Dalip; Kumar, N. Maruthi; Patel, Gautam; Gupta, Sudeep; Varma, Rajender S.; Tetrahedron Letters; vol. 52; 16; (2011); p. 1983 – 1986;,
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 14719-21-2 as follows. category: amides-buliding-blocks

Vl.j .dN-[3-(6-Benzyloxy-pyridazin-3-yl)-prop-2-vnyl1-2,2,2-trifluoro-acetamide; 16.7 g (50.0 mmol) Trifluoro-methanesulfonic acid 6-benzyloxy-pyridazin-3-yl ester and 15.1 g (100.0 mmol) 2,2,2-trifluoro-N-prop-2-ynyl-acetamide are dissolved in 150 ml THF and 75 ml triethyl amine. 1.4 g (2.0 mmol) bis-(triphenylphosphine)palladiumdichloride and 1.40 g (7.35 mmol) copper-(l)-iodide are added at -5C. The mixture is stirred for 20 hours at RT. After that time the solvent is evaporated. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried over sodium sulphate, the solvent is evaporated. The product is washed with tert-butyl methyl ether and dried at 80C. Yield: 9.50 g (57% of theory),Rf value: 0.50 (silica gel, methylene chloride/ethyl acetate = 5:1 ) M. p. 163-166C C-IeH-I2FsNsO2

According to the analysis of related databases, 14719-21-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/48802; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 147751-16-4, 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 147751-16-4 as follows.

LiAlH4 (9.0 mL of a 1 M solution in THF, 9.0 mmol) was added dropwise to a suspension of 2-ethylpyridine-3-carboxylic acid (500 mg, 3.31 mmol) in THF (5 mL) under N2 with cooling in an ice bath. The resulting solution was stirred for 1 hour, then quenched by the careful addition of water (0.35 mL) then aqueous NaOH (0.25 mL of a 15% w/v solution) then water (1 mL). After stirring for 10 minutes the mixture was filtered and the filtrate concentrated in vacuo to give a colourless oil (250 mg); MS m/z: 138 (M+H)+. This material was dissolved in DCM (10 mL) and tert-butyl N-methylsulfonylcarbamate (630 mg, 3.23 mmol) and PPh3 (950 mg, 3.62 mmol) were added followed by DEAD (500 muL, 3.04 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, then partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. After stirring for 5 minutes the organic phase was isolated using a phase separation cartridge. The solvent was removed in vacuo and the residue purified by column chromatography (silica, DCM-EtOAc elution) to give an oil that was taken up in HCl (10 mL of a 3 M solution in MeOH). PtO2 (150 mg, 0.66 mmol) was added and the mixture shaken in a Parr hydrogenator for 18 hours under 60 psi of H2 pressure. The reaction mixture was poured onto a pre-wetted ion-exchange cartridge, washing with MeOH then eluting the product with 2 M methanolic NH3 solution. The filtrate was concentrated in vacuo to give N-((2-ethylpiperidin-3- yl)methyl)methanesulfonamide A74 as a colourless oil (70 mg) that was taken directly on to the next reaction without further purification; MS m/z: 221 (M+H)+.

According to the analysis of related databases, 147751-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)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 6292-59-7, Safety of 4-(tert-Butyl)benzenesulfonamide

p-t-butyl benzene sulphonamide (2.2 g, 0.0104 mol) was taken in Dimethyl Sulphoxide and potassium carbonate was added (2.75 g, 0.0198 mol) under inter atmosphere and stirred for 0.5 h. 3.4 g of 4,6- dichloro 5-(2-methoxyphenoxy) [2,2]-bipyrimidinyl compound (formula-3) 3.44 g, 0.009 mol was added and heated to 120° C. and maintained at the same temperature for 2 h. The reaction mass was quenched in iN hydrochloric acid and stirred for 2 h. Product precipitates out and was filtered and washed with water and dried under vacuum yielding 4.3 g (9 6percent) of pale yellow crystalline solid 4,6- dichioro 5-(2-methoxyphenoxy) [2,2]- bipyrimidinyl compound of formula-3 having the X-ray diffraction pattern with peaks at 8.547, 9.867, 11.068, 11.97, 13.851, 14.726, 15.539, 17.213, 18.428, 20.463, 22.232, 22.704, 23.536,23.937, 24.827, 26.291, 26.545, 27.294, 27.815, 28.223,29.278, 30.022, 30.5, 31.447, 31.996, 32.454, 33.43, 33.644,34.251, 34.89, 35.662, 36.393, 37.402, 38.523, 39.022,40.238, 40.724, 41.35, 41.93, 43.732, 44.289, 45.24, 47.267, 47.978,49.123,49.438, 50.22, ±0.2 degrees two theta values.

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; Biocon Limited; Venkata, Srinivas Pullela; Kothakonda, Kiran Kumar; Rajmahendra, Shanmughasamy; Chandrasekaran, Indrajit; Kaliappan, Mariappan; Mailar, Rekha Shivappa; US2014/275535; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, 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: 4-Amino-N-phenylbenzenesulfonamide

Triethylamine (0.07 mL, 0.5 mmol) and phenyl isothiocyanate (2.1 mL, 11 mmol) were added sequentially to a solution of 4 (2.48 g, 10 mmol) in dry THF (10 mL). After heating under reflux for 48 h, all volatiles were removed under vacuum, and the resulting crude material was purified by flash chromatography on silica gel (hexanes/acetone, 3:1) to afford N-phenyl-4-[[(phenylamino)thioxomethyl]amino]benzenesulfonamide (5, also called LED209) (1.34 g, 35%) as a white solid, mp 160-162C. 1H NMR (CD3COCD3, 300 MHz) delta 9.35 (br s, 1H), 9.30 (br s, 1H), 8.98 (br s, 1H), 7.80-7.72 (m, 4H), 7.51-7.47 (m, 2H), 7.38-7.33 (m, 2H), 7.28-7.16 (m, 5H), 7.08-7.04 (m, 1H); 13C NMR (CD3COCD3, 75 MHz) delta 180.2, 143.9, 138.9, 138.2, 135.2, 129.3 (2C), 129.1 (2C), 127.9 (2C), 125.8, 124.6 (3C), 122.8 (2C), 120.8 (2C). Compound 27 was prepared in a similar manner as compound 3 in 90% yield; 1H NMR (CD3COCD3, 300 MHz) delta 9.63 (br s, 1H), 7.80-7.77 (m, 2H), 7.46-7.42 (m, 2H), 7.35-7.27 (m, 3H), 7.15-7.12 (m, 2H), 3.17 (s, 3H), 2.14 (s, 3H). Compound 8 was prepared in a similar manner as compound 4 in 65% yield; 1H NMR (CD3COCD3, 300 MHz) delta7.32-7.13 (m, 7H), 6.68-6.65 (m, 2H), 5.53 (br s, 2H), 3.10 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 127-77-5, its application will become more common.

Reference:
Patent; The Board of Regents of The University of Texas System; Omm Scientific, Inc.; SPERANDIO, Vanessa; FALCK, John R.; STEWART, Donald R.; (96 pag.)EP2219635; (2017); B1;,
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. 148890-63-5, name is 5-Amino-2H-benzo[b][1,4]oxazin-3(4H)-one, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Synthesis of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-sulfonyl chloride Into a 500 ml 3-necked round-bottom flask, was placed a solution of 5-amino-2H-benzo[b][1,4]oxazin-3(4H)-one (5 g, 28.96 mmol, 1.00 equiv 95%) in CH3CN (300 mL). To the above was added HOAc (24.9 g) dropwise with stirring, while cooling to a temperature of 0 C. To the above was added HCl (16.2 g, 36.5%) dropwise with stirring, while cooling to a temperature of 0 C. This was followed by the addition of a solution of NaNO2 (2.52 g, 36.52 mmol, 1.20 equiv) in H2O (2 mL), which was added dropwise with stirring, while cooling to a temperature of 0 C. The resulting solution was allowed to react with stirring, for 30 min while the temperature was maintained at 0 to 5 C. in a bath of H2O/ice. This was followed by and maintained with an atmosphere of sulfur dioxide, the resulting solution was allowed to react, with stirring, for an additional 2 h while the temperature was maintained at 0–5 C. in a bath of H2O/ice. To the mixture was added CuCl2.2H2O (5.11 g, 29.97 mmol, while cooling to a temperature of 0 to 5 C. The resulting solution was allowed to react, with stirring, maintained with an atmosphere of sulfur dioxide for an additional 2 h while the temperature was maintained at 0–5 C. in a bath of H2O/ice. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 25 C. The reaction progress was monitored by TLC (PE:EtOAc=1:1). The reaction mixture was then quenched by the adding 200 mL of H2O/ice. The resulting solution was extracted 3 times with 300 mL of dichloromethane and the organic layers combined. The resulting mixture was washed 5 times with 200 mL of brine. The mixture was dried over MgSO4. The residue was purified by eluding through a column with a 1:15 EtOAc/PE solvent system. This resulted in 0.9 g (11%) of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-sulfonyl chloride as a light yellow solid. LC-MS (ES, m/z): [M+C5H11N2-Cl]+ calcd for C13H17N3O4S 312, found 312 1H NMR (CDCl3, 300 MHz, delta): 9.06(1H,s), 7.69(1H,d), 7.36(1H,m), 7.18(1H,d), 4.75(2H),s)

The synthetic route of 148890-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; US2008/200471; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 6274-22-2,Some common heterocyclic compound, 6274-22-2, name is 4-Amino-N-methylbenzamide, molecular formula is C8H10N2O, 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 5 Method H: 4-(4-(5,6,7,8-tetrahydro-7,7-dimethyl-4-oxo-4H-thiazolo[5,4-c]azepin-2-yl)pyridin-2-ylamino)-N-methylbenzamide (I-5) 2-(2-chloropyridin-4-yl)-5,6,7,8-tetrahydro-7,7-dimethylthiazolo[5,4-c]azepin-4-one (70 mg, 1.0 Eq.), 4-amino-N-methyl-benzamide (41 mg, 1.2 Eq.), NaOtBu (61 mg, 2.8 Eq.), Pd(OAc)2 (5 mg, 0.1 Eq.) were suspended/dissolved in dry toluene and degassed (vacuum/N2 cycles*5). 2-Di-tert-butylphosphino)biphenyl (143 mg, 0.2 Eq.) was then added. The resultant mixture was then refluxed overnight. A further portion of NaOtBu (61 mg, 2.8 Eq.), Pd(OAc)2 (5 mg, 0.1 Eq.) and 2-(di-tert-butylphosphino)biphenyl (14 mg, 0.2 Eq.) were added, followed by dry dioxane (0.5 mL). The resultant mixture was refluxed for a further night. The reaction mixture was allowed to cool to RT, partitioned between EtOAc/MeOH (3:1)/NH4Cl, and then extracted into EtOAc/MeOH (3:1) (3*50 mL). The combined organic layers were washed with brine (1*20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was achieved using column chromatography (10% MeOH/90% DCM) to obtain the title compound as a bright yellow powder (18.6 mg, 19% yield); 1H NMR (DMSO D6) 1.0 (6H, s), 2.8 (3H, d), 3.0 (2H, s), 3.0 (2H, m), 7.3 (1H, m), 7.5 (1H, s), 7.8 (4H, s), 8.2 (1H, m), 8.3 (2H, m), 9.6 (1H, s); LC/MS M+1 (obs.) 422.20; LC/MS M-1 (obs.) 420.30.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-N-methylbenzamide, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US2009/281082; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 198211-38-0, 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. 198211-38-0, name is tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 21 Preparation of (4S,4aS,5aR,12aS)-9-((6-amino-3-azabicyclo[3.1.0]hexan-3-yl)methyl)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,1′-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride (the hydrochloride of Compound 26) In a 25 mL single-neck flask, Compound A (1 g) and tert-butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate (1 g) were dissolved in 5 mL of DMF, and reacted at room temperature for 0.5 h, 1.4 g of sodium triacetoxy borohydride was added slowly, and further reacted for 0.5 h. Then the reaction solution was mixed with 10 g of C18 fillers, packed into a column, separated by a quick preparative chromatography of ISCO (acetonitrile:water=1-10:100), collected the fraction which was confirmed by thin layer chromatography (TLC) to contain Compound 26. 10 mL of concentrated hydrochloric acid was added and stirred at room temperature for 0.5 h. After enrichment, the mixture was concentrated and freeze-dried to give hydrochloride of Compound 26 (58 mg, pale yellow powder). 1H NMR (D2O, 400 MHz) delta: 7.93 (s, 1H), 4.50 (m, 3H), 3.97 (s, 1H), 3.67 (br, 2H), 3.18 (s, 6H), 2.86-3.09 (m, 10H), 2.49 (t, 1H), 2.32 (s, 2H), 2.17 (d, 2H), 1.58 (m, 1H)

The synthetic route of tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP BIOSCIENCES CO., LTD.; Zhang, Hui; Dong, Yanyan; US2014/179638; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 6292-59-7, 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. 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of p-tert-butylbenzenesulfonamide (VI) (13.5 g, 63 mmol) was dissolved in sodium hydroxide solution (31.5 mL, 2N) and the solvent was distilled off under reduced pressure to give the sodium salt of p-tert-butylbenzenesulfonamide.A solution of tert-butylbenzenesulfonamide sodium and 4,6-dichloro-5- (2-methoxyphenoxy) -2,2 ‘-bipyridine (V) (21.05 g, 60.3 mmol) (200 mL) and heated to 90 ° C with stirring for 3 h. TLC was complete. The residue was diluted with IN hydrochloric acid and the pH was adjusted to 3 to 4 with IN hydrochloric acid. The crystals were recrystallized and dried under reduced pressure to give 29.5 g of a white solid as N- [6-chloro (2-methoxyphenoxy) [2,2 ‘] – dipyridyl] -4-yl] -4- (1,1-dimethylethyl) -benzenesulfonamide (W) The yield was 93percent.

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, 4-(tert-Butyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Tianci International Pharmaceutical Co., Ltd.; Li Xinjuanzi; Li Jianzhi; Ma Xilai; Chi Wangzhou; Liu Hai; Hu Xuhua; Zheng Xiaoli; Zhai Zhijun; Li Jianxun; (14 pag.)CN104193687; (2017); B;,
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. 118684-31-4, name is tert-Butyl (3-(hydroxymethyl)phenyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Comp nd 14B: tert-but l 3-form l hen l carbamate Compound 14A (13.8 g, 61.81 mmol, 1.00 equiv) was dissolved in DCE (400 mL) and Mn02 (54 g, 621.14 mmol, 10.05 equiv) was then added. The mixture was left under agitation at ambient temperature for 3 days after which the solids were removed by filtering. The filtrate was evaporated to dryness and the residue was purified on a silica column with a mixture of EtOAc and PE (1 :30) to yield 3 g (22 %) of compound 14B in the form of a white solid.

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; PIERRE FABRE MEDICAMENT; RILATT, Ian; PEREZ, Michel; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; HAEUW, Jean-Francois; WO2015/162293; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics