Tag: M.W=100-200

2623-33-8, 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 2623-33-8 as follows.

General procedure: A 10 mL Schlenk tube equipped with a magnetic stirrer was charged with [Rh Cp* Cl2]2 (5 mol%), AgSbF6 (20 mol%), Cu(OAc)2 (1equiv), Ag2CO3(1equiv),and substituted acetanilideas 1 (0.2 mmol). The tube wasevacuated and backfilled with argon for three times. Then allyl carbonate (0.4 mmol) in dioxane (1 mL) was added. After addition of all substrates, the reactionmixture was stirred and heated at 110Cfor 24h. Then reaction was cooled to room temperature. Solvent and volatile reagents were removed by rotary evaporation and theresidue was purified by flash column chromatography on silica gel to give the target product

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

Reference:
Article; Gong, Tian-Jun; Cheng, Wan-Min; Su, Wei; Xiao, Bin; Fu, Yao; Tetrahedron Letters; vol. 55; 11; (2014); p. 1859 – 1862;,
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1746-77-6, These common heterocyclic compound, 1746-77-6, name is Isopropyl 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.

Intermediate 491 -methylethyl (2E)-2-butenoylcarbamateIsopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to – 30C. When the solution temperature reached -17C 1 M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10C and -18C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0C. Diethyl ether (450ml) and 1 M HCI (375ml) were added and the mixture brought to 20C with vigourous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375ml) was added and the mixture stirred vigourously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1 :1 to 0:1 , 10CV). The product containing fractions were evaporated to dryness and loaded on to a 1500g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt = 0.68 , MH+ = 172

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 1746-77-6.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
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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. 4664-01-1 name is 3,4-Pyridinedicarboximide, 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. 4664-01-1

NaOH (10% aqueous, 640 ml) was cooled to 7 C. and bromine (15 ml, 286.82 mmol) added dropwise. Pyrrolo[3,4-c]pyridine-1,3-dione (41.711 g, 281.6 mmol) was then added to the reaction mixture before it was heated to 80 C. for 30 minutes. After this time the reaction was allowed to warm to 37 C. and the pH modified to 5.5 by the addition of acetic acid (70 ml). A suspension formed that was removed by filtration and washed with 20 ml of ice cold methanol to give the title compound (26.58 g, 68.33%) in a suitably clean form to be used without any further purification. m/z (LC-MS, ESP): 139 [M+H]+, R/T=0.72 mins.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Pyridinedicarboximide, and friends who are interested can also refer to it.

Reference:
Patent; Kudos Pharmaceuticals Ltd; US2006/199804; (2006); A1;,
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16982-21-1, 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 16982-21-1 as follows.

To a boiling solution of ethyl thiooxamate (13,3 g ,10Og, 100 mmol) in ethanol (100 mL) was added l-bromo-3-methylbutan-2-one (17,6 g ,g, 106 mmol) dropwise during 15 minutes. The solution was refluxed for one hour. The solution was added to 250 mL of ice-cold water and basified with concentrated ammonia solution. This mixture was extracted twice with AcOEtethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by column chromatography with dichloromethane to dichloromethane with 2% MeOH methanol to give 13,1 g (65%) of the target product: 1H-NMR-CDCl3: 7,20 (s, IH), 4,49 (m, 2H), 3,25 (m, IH), 1,42 (t, 3H), 1,35 (d, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 16982-21-1, and friends who are interested can also refer to it.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14921; (2007); A1;,
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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,
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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;,
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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;,
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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;,
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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