Author: tianli

17193-28-1, These common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one-monohydrochloride 20 g (0.156 mol) of 1-aminocyclopentane-1-carboxamide and 31 g (0.19 mol) of trimethyl orthovalerate are refluxed at 70-80 C. inner temperature for 1 hour. The condenser is then changed to a “No hold up” condenser, while heating and stirring are continued to distille off volatile components. The reaction is completed in vacuo. The residue is dissolved in 150 ml of acetone the pH is adjusted to 1-2, after cooling the resulting suspension the product is filtered off. 31 g of the title compound is obtained, yield 86.4%. IR: 3600-2200: vibr, NH; 1779: gammac=o; 1642 gammac, 1517: deltaNH (IRFT Perkin Elmer)

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 17193-28-1.

Reference:
Patent; Sanofi-Synthelabo; US6162923; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, 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 2-(2-aminoethoxy)ethylcarbamate (570 mg, 2.8 mmol) was taken up in CH3CN (8 mL) and DMF (8 mL) along with Acipimox (435 mg, 2.8 mmol) HATU (1.17 g, 3.1 mmol) and DIEA (730 muL, 4.2 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (50 mL), washed with water (3*10 mL), brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 5-((2-(2-((tert-butoxycarbonyl)amino)ethoxy) ethyl)carbamoyl)-2-methylpyrazine 1-oxide (810 mg, 85%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82156; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 283173-80-8, name is 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-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 283173-80-8, 283173-80-8

l, r-Bis(diphenylphosphino)ferrocene palladium (II) dichloride (2.5 moles, 1.83 kg) was added to a solution of Formula-Al (1.0 moles) in a 1:2 mixture of 4.2 L of dichloromethane and degassed dimethylacetamide. The reaction mass was stirred for 1 hour at about 20 C. Thereafter, the reaction mixture temperature was raised to 95 C and stirred for 1 hour. In a separate vessel, Formula-C3 (1.2 moles) was dissolved in dimethylacetamide (1.1 L) and added to 2.8 L of an aqueous solution of sodium carbonate (2.0 moles) and stirred for 3 hours at 20 C. The contents of the separate vessel were added to the first reaction mixture, maintaining the temperature above 90 C. The combined reaction mixture was stirred for 2 hours, cooled to room temperature, and further stirred for 4 hours. Water (2.8 L) was added to the reaction mixture which was filtered. The obtained solid was crystallized in methanol to obtain a compound of Formula-B 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, 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MYLAN LABORATORIES LTD; JAYACHANDRA, Sureshbabu; SETHI, Madhuresh; KAUSHIK, Vipin Kumar; RAVI, Vijaya, Krishna; TELAGAMSETTY, Bhaskar Kumar; (44 pag.)WO2019/130229; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

631-58-3, 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. 631-58-3, name is Propanethioamide, This compound has unique chemical properties. The synthetic route is as follows.

Example 11 2-ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole A solution of 2-bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrobromide (11 g, 29 mmol) and thiopropionamide (2.7 g, 30 mmol) in N,N-dimethylformamide (30 mL) was stirred for 14 hours at room temperature. Aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, then, the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to obtain a title compound (3.3 g, yield 38%). Oil 1H-NMR (CDCl3) delta: 1.64 (3H, t, J=7.6 Hz), 2.34 (3H, s), 3.10 (2H, q, J=7.6 Hz), 6.84-6.86 (1H, m), 7.05-7.09 (1H, m), 7.13-7.25 (3H, m), 7.37 (1H, s), 8.10 (1H, d, J=5.6 Hz).

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; Ohkawa, Shigenori; Naruo, Ken-ichi; Miwatashi, Seiji; Kimura, Hiroyuki; US2004/53973; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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 67442-07-3. 67442-07-3

into the reactor add LD-I and tetrahydrofuran; Replace nitrogen 3 times, under nitrogen protection, cool the solution at-12 C, slowly add 2N iso-propylmagnesium chloride THF solution, the resulting reaction solution is stirred at -12C for 1h, until the reaction is complete, dissolve 2-chloro-N-methoxyl-N-methylacetamide into methyl tert-butyl ether, after that slowly add 2-chloro-N-methoxyl-N-methylacetamide solution into the reactor, while dropping, keep the internal temperature at -10C, adjust the internal temperature at 0C and continue stirring for 2 hours, after the reaction is completed, 1N hydrochloric acid is added and the layers are separated, and extracting the aqueous layer with methyl tert-butyl ether, combining organic layers, concentrate under reduced pressure at 10 volumes, adjust the temperature at 20 C, and stir for 1.5h, centrifuge, and wash the filter cake with isopropyl alcohol, dried, and obtained solid product LD-J.

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 2-Chloro-N-methoxy-N-methylacetamide.

Reference:
Patent; Anhui Nuoquan Pharmaceutical Co., Ltd.; Du Xiaopeng; Xu Liangzhi; Hu Zhigang; He Darong; Qian Zhujin; He Yong; Liu Zhuangzi; (12 pag.)CN107879908; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6331-71-1, A common heterocyclic compound, 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, molecular formula is C9H12N2O, 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 3: Synthesis of methyl 5-(N-(4- (dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylate (Intermediate 75) To a solution of 4-amino-N,N-dimethylbenzamide (Int. 74) (57 g, 347 mmol) in pyridine (570 L, 7.06 mmol) kept at 0 degrees in an ice/water bath, methyl 5-(chlorosulfonyl)thiophene-2-carboxylate (100 g, 417 mmol) was added and the mixture stirred at 0 degrees for 3hr. The reaction mixture was diluted with HCl IN and extracted with AcOEt (x2). The organic phase was dried over Na2SO4 and concentrated under vacuum to give 100 mg of 5-(N-(4- (dimethy lc arb amoy l)pheny 1) sulf amoy l)thiophene -2 -carb oxy late (Int . 75).

The synthetic route of 6331-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; ARMANI, Elisabetta; CAPALDI, Carmelida; CARZANIGA, Laura; ESPOSITO, Oriana; WO2013/182451; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1, These common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, 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 mixture of Trifluoroacetamide (1.2 g, 10.6 mmol), Lawesson’s reagent (2.36 g, 5.84 mmol) and THF (10 mL) was heated at reflux for 2 h.The mixture was concentrated and purified by chromatography to give the sub-title compound (0.89 g, 6.9 mmol, 65 %).

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 354-38-1.

Reference:
Patent; ATROGI AB; PELCMAN, Benjamin; BENGTSSON, Tore; (93 pag.)WO2019/53427; (2019); A1;,
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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., 67442-07-3

(d) To a solution of 0.33 g (0.83 mmol) 3-acetoxy-4-fluoro-N-[4-(imidazol-1-yl)-3-trifluoromethylphenyl]-benzamide, J-1c, in 5 mL acetone and 0.5 mL of methanol was added cesium carbonate (0.54 g, 1.65 mmol) and 2-chloro-N-methoxy-N-methyl-acetamide (0.15 g, 1.07 mmol) and the resulting mixture was stirred for 6 h at 45¡ã C. After cooling to room temperature, the mixture was partitioned between ethyl acetate and sat. brine (2*20 mL). The organic layer was filtered though a silica gel plug and concentrated. The residue was purified by titurated with diethyl ether (2*20 mL) to give 0.35 g (92percent) of 4-fluoro-N-[4-(imidazol-1-yl)-3-trifluoromethylphenyl]-3-[(N-methoxy-N-methylcarbamoyl)methoxy]benzamide, J-1d, as a white solid: Rt=11.95 min.; 1H NMR (300 MHz, CDCl3) delta8.34 (d, 1H, J=2.4 Hz), 8.11 (dd, lh, J=8.7 Hz), 7.64-7.54 (m, 3H), 7.42 (d, 1H, J=8.7 Hz), 7.22-7.15 (m, 2H), 6.97 (s, 1H), 502 (s, 2H), 3.72 (s, 3H), 3.06 (s, 3H); MS (ESI): Calculated for C21H18F4N4O4 (M+H+): 467, Found: 467.

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; Bender, Steven Lee; Bhumralkar, Dilip; Collins, Michael Raymond; Cripps, Stephen James; Deal, Judith Gail; Jia, Lei; Nambu, Mitchell David; Palmer, Cynthia Louise; Peng, Zhengwei; Varney, Michael David; US2002/103203; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

711007-44-2, 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. 711007-44-2, name is 2,3-Diaminobenzamide, A new synthetic method of this compound is introduced below.

Example 90G 2-((1R,5S)-6-((S)-1-phenylethyl)-6-azabicyclo[3.2.1]octan-5-yl)-1H-benzo[d]imidazole-4-carboxylic acid A mixture of (1R,5S)-6-((S)-1-phenylethyl)-6-azabicyclo[3.2.1]octane-5-carbaldehyde (2.0 g, 8.2 mmol), 2,3-diaminobenzamide (1.85 g, 8.2 mmol) and KHSO3 (2.14 g, 20.6 mmol) in DMA (30 mL) was stirred at 140 C. for 17 h. The reaction mixture was poured into ice. The resulting mixture was extracted with ethyl acetate three times. The combined organic layers were washed brine twice and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by column (silica gel, Hex/EtOAc/HOAc=2:1:0.01) to yield 2-((1R,5S)-6-((S)-1-phenylethyl)-6-azabicyclo[3.2.1]octan-5-yl)-1H-benzo[d]imidazole-4-carboxylic acid (930 mg, 30%). 1H NMR (DMSO, 400 MHz), delta: 10.9~11.2 (s,1H), 7.72~7.80 (m, 1H), 7.80~7.90 (m, 1H), 7.40~7.58 (m, 2H), 7.19~7.40 (m, 4H), 3.95~4.05 (m, 1H), 3.12~3.23 (m, 1H), 2.22~2.46 (m, 4H), 1.68[1.88 (m, 2H), 1.42~1.59 (m, 2H), 1.15~1.26 (m, 2H), 0.69~0.80 (m, 3H).

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; LEAD THERAPEUTICS, INC.; US2009/62268; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 20348-09-8 name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 20348-09-8

Step 1. 7-Bromo-2H-pyrido[3,2-b]1,4-oxazin-3(4H)-one To a solution of 5.6 g 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and the mixture is chilled The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried under vacuum at 70 C. and then used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Rorer Pharmaceutical Corporation; US4906629; (1990); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics