Amides-buliding-blocks

Reference of 147291-66-5, These common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, 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.

10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 155 mg, 0.55 mmol), tert-butyl N-[(3-aminophenyl)methyl]carbamate (Chembasics, 111 mg, 0.50 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27 mg, 0.05 mmol) were dissolved in 1,4-dioxane (7.5 mL) Caesium carbonate (326 mg, 1.0 mmol) was added and the mixture purged with a stream of nitrogen for 5 minutes.Tris(dibenzylideneacetone) palladium (II) (28 mg, 0.03 mmol) was added and the apparatus was evacuated and backfilled with nitrogen (×3) and then heated at 100 C. for 8 h. The mixture was cooled, filtered and the filtrate absorbed onto an SCX-3 column, washed with methanol and the product eluted with ammonia in methanol. Product containing fractions were concentrated and purified by normal phase chromatography (1% methanol/DCM) to give the title compound as a white solid (57 mg, 24%).1H NMR (399.9 MHz, DMSO-d6) delta1.41 (9H, s), 1.59-1.71 (6H, m), 1.96 (2H, m), 2.58 (2H, m), 3.17 (3H, s), 3.61 (2H, m), 4.09 (2H, d), 4.85 (1H, m), 6.80 (1H, d), 7.18 (1H, t), 7.30 (1H, t), 7.57 (1H, d), 7.62 (1H, s), 8.04 (1H, s), 9.16 (1H, s); MS m/z 467 [M+H]+.

Statistics shows that tert-Butyl 3-aminobenzylcarbamate is playing an increasingly important role. we look forward to future research findings about 147291-66-5.

Reference:
Patent; ASTRAZENECA AB; US2008/9482; (2008); A1;,
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. 154350-29-5, name is Cyclopropanesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 154350-29-5

14-tert-Butoxycarbonylamino-18-(tert-butyl-dimethyl-silanyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid (500 mg, 0.86 mmoL) was dissolved in 25 mL of THF and treated with CDI (180 mg, 1.12 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere). After refluxing the reaction mixture for 2 h, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (135 mg, 1.12 mmoL) and DBU (170 mg, 1.12 mmoL). The reaction mixture was stirred for 4 h at rt, and the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and pH 4 buffer. The organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product. It was then purified by flash chromatography (eluding with 33percent ethyl acetate in hexane) to give 300 mg (51percent) of [18-(tert-butyl-dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester as a white solid. 1H NMR (300 MHz, CD3OD) delta 1H 0.07 (s, 3 H), 0.08 (s, 3 H), 0.85 (s, 9 H), 0.87-1.49 (m, 21 H), 1.73-1.95 (m, 3 H), 2.08-2.16 (m, 1 H), 2.25-2.36 (m, 2 H), 2.42-2.56 (m, 1 H), 2.85-2.93 (m, 1 H), 3.65-3.74(dd, J=10.61, 3.66 Hz, 1 H), 3.89 (d, J=10.25 Hz, 1 H), 4.34 (m, J=9.70, 9.70 Hz, 1 H), 4.43 (t, J=7.87 Hz, 1 H), 4.57 (s, 1 H), 4.94-5.01 (m, 1 H), 5.10 (d, J=8.78 Hz, 1 H), 5.66-5.75 (m, 1 H), 6.55 (s, 1 H), 10.13 (s, 1 H); MS m/z 683 (M++1).

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; Bristol-Myers Squibb Company; US2007/93414; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1237535-78-2, The chemical industry reduces the impact on the environment during synthesis 1237535-78-2, name is 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one, I believe this compound will play a more active role in future production and life.

Example 2: Synthesis of compounds 2.1-2.37 Step A: (1S,1aS,6bR)-5-((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-4-yl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylic acid ethyl ester Intermediate III (400mg, 1.8mmol), 5-fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one (250mg, 1.5mmol), and cesium carbonate (801mg, 2.3mol) in DMF (20mL) was stirred at 120C for 2 hours. The reaction mixture was washed with water (10mL). The reaction was diluted and extracted with ethyl acetate (2 × 10mL). The combined organic extracts were washed with brine (20mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (PE:EtOAc = 3:1 elution) to give the target compound as a white solid (360mg, 54.6%).

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, 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BeiGene, Ltd.; Zhou, Changyou; Wang, Shaohui; Zhang, Guoliang; (104 pag.)CN105348299; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 53297-68-0, A common heterocyclic compound, 53297-68-0, name is 2-Chloro-4-sulfamoylaniline, molecular formula is C6H7ClN2O2S, 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 the carboxylic acid and aniline shown above, in pyridine at O0C, was added POCl3 dropwise for 5 min. The reaction was complete after stirring at O0C for an additional 50 min. The reaction mixture was quenched by addition Of H2O (1 mL), then concentrated in vacuo to light brown oil which was diluted with CH2Cl2 (200 ml). The organic layer was washed with H2O (1 x 50 ml), saturated NaHCO3 solution (1 x 50 ml), then brine (1 x 50 ml). The organic solution was dried over Na2SO4 and concentrated to dryness. The resulting oil was triturated with EtOH to give light yellow solid. To the mixture was added H2O to collect more solid. The light yellow solid was collected by vacuum filtration and dried under high vacuum for 16 hrs to yield 930 mg (72%) of product. Additional product (132 mg, 10%) was recovered by extraction of the filtrate with CH2Cl2 followed by column chromatography with acetone/CH2Cl2 (20:80).

The synthetic route of 53297-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/26356; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 121-30-2, A common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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 2,4-disulfamyl-5-chloroaniline (15c, 3 g, 10 mmol) in acetonitrile (120 mL) at 40 C was slowly added concd sulfuric acid (13.5 mL). After 30 min, to the solution was added sodium nitrite (1.32 g, 19.1 mmol) portionwise. The solution was stirred at 0 C for 1 h, to which was then added a solution of CuBr2 (2.46 g, 11 mmol) in water (2 mL) in portions. After 1.5 h, the reaction mixture was warmed to room temperature and then heated to 80 C to evolve nitrogen gas. When no further gas was generated, the solution was concentrated. Purification by flash column chromatography on a silica gel column with hexane/EtOAc (1:1) provided a pale yellowish solid 16c in 62% yield. Mp 291-292 C (lit:refPreviewPlaceHolder25 290 C). 1H NMR (400 MHz, acetone-d6) delta 8.67 (s, 1H; ArH), 8.36 (s, 1H; ArH), 7.03 (br, 4 H; SO2NH2). 13C NMR (100 MHz, acetone-d6) delta 145.0, 144.1, 140.7, 134.0, 128.8, 96.7.

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; Tan, Chen-Ming; Chen, Grace Shiahuy; Chen, Chien-Shu; Chang, Pei-Teh; Chern, Ji-Wang; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6316 – 6328;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 103361-99-5, name is 7-Fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C8H6FNO2, 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. SDS of cas: 103361-99-5

c. 7-fluoro-4-isobutyl-2H-1,4-benzoxazin-3(4H)-one To 3.96 g (99 mmol) of hexanes washed 60% sodium hydride in 150 ml of N,N-dimethylformamide was added portionwise as a solid 15 g (90 mmol) of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one. When the addition was complete the reaction was stirred at room temperature for 10 min, after which time 19.8 g (108 mmol) of isobutyl iodide was added. The reaction was then stirred overnight before quenching into 200 ml of water. The aqueous phase was extracted with EtOAc (2*150 ml) and the combined organics were dried over Na2 SO4, filtered and evaporated in vacuo to give the desired alkylated product, as a yellow oil (13 g, 65% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103361-99-5, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US5393735; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 402-46-0, These common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, 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.

Step b N-[(1-Oxo-2-oxo-2-chloro)ethyl]-4-(fluoro)benzenesulfonamide Combine 4-(fluoro)benzenesulfonamide (1.12g, 6.4mmol) and oxalyl chloride (15mL) and reflux for 9 hours. Evaporate the excess oxalyl chloride in vacuo to give the title compound.

Statistics shows that 4-Fluorobenzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 402-46-0.

Reference:
Patent; Merrell Pharmaceuticals Inc.; US5606063; (1997); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 16091-26-2,Some common heterocyclic compound, 16091-26-2, name is 3′-Aminobenzanilide, molecular formula is C13H12N2O, 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.

In a 250 mL three-necked flask equipped with a stirrer, a thermometer and a reflux condenser (with a water separator), 130.0 g of methyl chloroacetate was added.42.4 g of m-anilinoaniline was added under stirring.24.5 g of sodium carbonate was uniformly mixed under stirring, and the temperature was raised to 100 to 105 C, and refluxed for 2.0 h. 4.2 g of potassium bromide and 0.3 g of zinc powder were added, and the mixture was refluxed at 110 to 130 C for 3.0 h. The sample was sampled and detected by high pressure liquid chromatography, and the purity of the target product was 99.2%. After methyl chloroacetate was distilled off under reduced pressure, acetic acid was added to obtain an acetic acid solution of m-benzoylamino-N,N-di(methyl acetate) aniline in a yield of 98.4%.

The synthetic route of 16091-26-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central South University of Forestry and Technology; Zhao Ying; Hu Renjie; Xiong Yuanfu; Zhao Qi; Yuan Yao; Tan Xiaoyan; (8 pag.)CN109796365; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 120157-97-3, A common heterocyclic compound, 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, molecular formula is C13H18BrNO2, 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: A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 3-fluorophenylboronic acid (0.56?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol), Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14d as a white solid (0.52?g, 62%); Rf?=?0.00 (EtOAc 9: acetone 1): 1H NMR (DMSO-d6, 400?MHz) delta 2.98-3.09 (m, NH3CH2CH2), 7.17-7.52 (m, 6 ArH), 7.68 (d, J?=?8.0?Hz, 2 ArH), 8.34 (s, NH3); 13C NMR (DMSO-d6, 100?MHz) delta 33.0 (NCH2CH2), 113.6 (d, JC-F?=?21.8?Hz), 114.5 (d, JC-F?=?20.9?Hz), 123.0 (d, JC-F?=?2.4?Hz), 127.4, 129.8, 131.3 (d, JC-F?=?8.5?Hz), 137.6 (d, JC-F?=?2.1?Hz), 137.9, 142.8 (d, JC-F?=?7.7?Hz), 163.2 (d, JC-F?=?241.7?Hz) (12 ArC).

The synthetic route of 120157-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yeon, Seul Ki; Choi, Ji Won; Park, Jong-Hyun; Lee, Ye Rim; Kim, Hyeon Jeong; Shin, Su Jeong; Jang, Bo Ko; Kim, Siwon; Bahn, Yong-Sun; Han, Gyoonhee; Lee, Yong Sup; Pae, Ae Nim; Park, Ki Duk; Bioorganic and Medicinal Chemistry; vol. 26; 1; (2018); p. 232 – 244;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 63920-73-0, 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. 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-picolinaldehyde (13.10 g, 32.46 mmol) and 2-amino-4,6-dimethoxybenzamide (6.68 g, 34.08 mmol) in N,N-dimethylacetamide (150 ml) was added NaHSO3 (8.90 g, 48.69 mmol) and p-toluenesulfonic acid monohydrate (6.17 g, 32.46 mmol). The reaction mixture was stirred at 120 C. for 14 h. After that time the reaction was cooled to rt, concentrated under reduced pressure, diluted with saturated Na2CO3 (150 mL) and the precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was washed with diethyl ether and dried to give 2-(5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-(methylthio)phenyl)-pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (17.38 g, 92%) as light yellow solid: ESI MS m/z 580 [M+H]+.

The synthetic route of 2-Amino-4,6-dimethoxybenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; Fairfax, David John; Martin, Gregory Scott; Quinn, John Frederick; Duffy, Bryan Cordell; Wagner, Gregory Steven; Young, Peter Ronald; US2014/140956; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics