Tag: M.W=100-200

Related Products of 90-16-4,Some common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, molecular formula is C7H5N3O, 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 the triazin-4(3H)-one (1.0 mmol), phenylboronic acid (1.5 mmol), anhydrous Cu(OAc)2 (1.0 mmol) and Et3N (2.0 mmol) in ClCH2CH2Cl (10-15 mL) was stirred at ambient temperature for 1.0-2.0 h. Progress of the reaction was monitored by TLC. The reaction mixture was filtered through celite. The filtrate was collected, concentrated in vacuo, and the residue was purified by chromatography on silica gel using hexane/ethyl acetate to afford the desired product.

The synthetic route of 90-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shiva Kumar; Adepu, Raju; Sandra, Sandhya; Rambabu; Rama Krishna; Malla Reddy; Misra, Parimal; Pal, Manojit; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1146 – 1150;,
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Synthetic Route of 14658-93-6, These common heterocyclic compound, 14658-93-6, name is 2-Hydroxy-N,N-dimethylacetamide, 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.

6.2a) dimethylcarbamoylmethyl 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]propionyl}-1,4′-bipiperidinyl-4-carboxylate 30 mg (0.29 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added at RT to a solution of 200 mg (0.25 mmol) 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4′-bipiperidinyl-4-carboxylic acid (Example 6.1a), 90 mg (0.28 mmol) TBTU and 80 muL (3.73 mmol) triethylamine in 1.8 mL DMF and this was stirred for 20 h at RT. The reaction mixture was poured onto saturated NaHCO3 solution, the precipitate formed was suction filtered and dried. Further purification was carried out by HPLC, the fractions containing the product were combined and lyophilised. Yield: 100 mg (47% of theory) ESI-MS: (M+H)+=851 Retention time (HPLC-MS): 3.9 min (method B)

The synthetic route of 14658-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mueller, Stephan Georg; Rudolf, Klaus; Lustenberger, Philipp; Stenkamp, Dirk; Santagostino, Marco; Paleari, Fabio; Doods, Henri; Arndt, Kirsten; Schaenzle, Gerhard; US2007/72847; (2007); A1;,
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Synthetic Route of 1120-16-7, These common heterocyclic compound, 1120-16-7, name is Dodecanamide, 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.

Under argon atmosphere, 60.04 mmol of catalyst Nd2Na8 (OCH2CF3) 14 (THF), 1 mmol of lauric amide and 1.2 mmol of benzylamine were added into the reaction flask treated with dehydration and deoxygenation under argon atmosphere, and the mixture was stirred at 120 C. for 16 hours. The reaction was completed The reaction mixture was extracted with dichloromethane, extracted three times, and the organic phase was dried over anhydrous sodium sulfate. The solvent was drained and the residue was subjected to column chromatography (eluent: petroleum ether: ethyl acetate = 6: 1) to give The target product, N-benzyl lauramide, is a colorless solid in 90% yield.

Statistics shows that Dodecanamide is playing an increasingly important role. we look forward to future research findings about 1120-16-7.

Reference:
Patent; Anhui University; Sheng Hongting; Zeng Ruijie; Feng Yan; Zhu Manzhou; (10 pag.)CN104961777; (2017); B;,
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Electric Literature of 7150-72-3, A common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 4.

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; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
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1565-17-9, name is 4-Acetylbenzenesulfonamide, 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. Product Details of 1565-17-9

To 4-aminosulfonylacetophenone (2.5 g) in 1,4-dioxane (30 ml) solution, N,N-dimethylformamide dimethylacetal (30 ml) was added and the mixture was stirred at 90C for 24 hours. The precipitate was collected by filtration and washed with ethyl acetate to obtain the title compound (3 g).

The synthetic route of 1565-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP1820798; (2007); A1;,
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Some common heterocyclic compound, 78888-18-3, name is tert-Butyl allylcarbamate, molecular formula is C8H15NO2, 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. category: amides-buliding-blocks

Sodium hydride (768 mg of 60% dispersion in mineral oil, 19.2 mmol) was washed twice with 15 mL portions of hexane and suspended in 15 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl allylcarbamate (1.0 g, 6.4 mmol) was added dropwise. Reaction mixture was warmed up to room temperature and stirred under argon for 30 min. Reaction mixture was cooled to 0C and freshly distilled ethyl iodide (1.02 mL, 12.8 mmol) was added dropwise. Reaction mixture was allowed to warm up to room temperature overnight, and it was then cooled to 0C and quenched with saturated ammonium chloride solution. The layers were separated and aqueous layer was extracted with Et2O. Organics were combined and washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Crude reaction mixture was purified by flash column chromatography (hexanes:EtOAc 4:1) to give 1.0g (85%) of the title compound as a colorless oil. IR (neat) 3083, 3010, 2979, 2933, 2249, 1682 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.03-1.07 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 3.20 (br m, 2H), 3.77 (br m, 2H), 5.05-5.11 (m, 2H), 5.68-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 12.59, 27.55, 40.39, 48.19, 78.31, 115.10, 133.67, 154.46; m/z (relative intensity) 185(1), 129(25), 112(9), 84(10), 70(30), 57(100), 41(65), 29(25). Anal.Calcd. for C10H19NO2: C, 64.83; H, 10.34; O, 17.24. Found: C, 64.67; H, 10.60; O, 17.31.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 78888-18-3, its application will become more common.

Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
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Application of 70-55-3, 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. 70-55-3 name is 4-Methylbenzenesulfonamide, 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.

General procedure: In a round-bottom flask, a benzyl alcohol 2 (1.0 mmol), a sulfonamide1 (1.8 mmol) and BF3·OEt2 (151 muL, 1.2 mmol) were dissolved in CHCl3 (2.0 mL). The mixture was stirred for 2 h under reflux in air atmosphere, then the solvent was removed under reduced pressure using a rotary evaporator. The product was isolated by column chromatography of the residue on silica gel (EtOAc-PE, 1:10 to 1:2, v/v) to give the desired mono- and di-N-benzylated products 3 and 4.

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

Reference:
Article; Pan, Jing; Li, Jia-Qiang; Huang, Ruo-Feng; Zhang, Xiao-Hui; Shen, Hang; Xiong, Yan; Zhu, Xiang-Ming; Synthesis; vol. 47; 8; (2015); p. 1101 – 1108;,
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Reference of 57561-39-4, 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 57561-39-4 as follows.

To a solution (50 mL) of tert-butyl 2-hydroxyethyl(methyl)carbamate (3.50 g) obtained in Reference Example 1, thioacetic acid (1.72 mL) and triphenylphosphine (7.87 g) in tetrahydrofuran was dropwise added slowly a solution (10 mL) of diisopropyl azodicarboxylate (5.91 mL) in tetrahydrofuran under ice-cooling. The mixture was stirred under ice-cooling for 1 hr. and at room temperature for 2 hrs. The reaction mixture was again ice-cooled and a solution (10 mL) of triphenylphosphine (7.87 g) and diisopropyl azodicarboxylate (5.91 mL) in tetrahydrofuran was added. The mixture was stirred under ice-cooling for 30 min. Thioacetic acid (1.14 mL) was added and the mixture was stirred under ice-cooling for 30 min. and at room temperature overnight. The reaction mixture was concentrated under reduced pressure and hexane and diisopropyl ether were added to the residue. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. This step was repeated and a saturated aqueous sodium hydrogen carbonate solution (50 mL) was added. The mixture was extracted with ethyl acetate (100 mL). The ethyl acetate layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate_hexane=5:95, and then 15:85). A 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the purified product (4.47 g) and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and ethyl acetate and diethyl ether were added to the residue for crystallization to give the title compound (1.79 g) as a pale-yellow solid.1H-NMR (DMSO-d6) : 2.38(3H,s), 2.52 (3H, s), 2.96-3.08(2H,m), 3.12-3.20(2H,m), 9.35(2H,br).

According to the analysis of related databases, 57561-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
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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. 148017-28-1, name is tert-Butyl sulfamoylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: tert-Butyl sulfamoylcarbamate

(S)-(6-chloro-2,3-dihydrobenzo[b][1 ,4]dioxin-2-yl)methanol (20.0 g, 100.0 mmol, 1 .0 eq.), tert-butoxycarbonyl sulfamide (27.4 g, 140.0 mmol, 1 .4 eq) and triphenylphosphine (3.9 g, 1 18.0 mmol, 1 .2 eq,) were dissolved in MTBE (140 g) and the resulting mixture was warmed under stirring to a temperature in the range of 27-32C. Diisopropyl-azodicarboxylate (22.6 g, 1 1 1 .0 mmol, 1 .1 1 eq) in MTBE (18 g) was added dropwise over about 60-120 min, while maintaining the temperature of the reaction mixture in the range of about 27-32C. The resulting mixture was then stirred for 2-6 hours, cooled to a temperature in the range of about 15-20C. The resulting mixture was then seeded with triphenylphosphinoxide and bis-1,2-(isopropoxycarbonyl)-hydrazine (which were taken from previously prepared batches) and stirred for an additional hour. After the onset of crystallization was confirmed, n-hexane (80 g) was added over about 45-60 min, after which time, the resulting suspension was stirred for an additional 120 min at a temperature of about 15-20C. The resulting mixture was then cooled to a temperature in the range of -15 to -10C and stirred for about 4-6 hours. The resulting off-white solid was filtered off and washed with a cold mixture of MTBE (20 g) and n-hexane (10 g). At 50C and a pressure of about 450-400 mbar a total of 240 g of solvent was distilled off from the resulting filtrate. To the resulting concentrated residue were added toluene (100 g) and n-hexane (15 g). The resulting solution, at a temperature of about 22-27C, was washed with a mixture of methanol (40 g) and water (60 g). This step was then repeated twice (2X). At a temperature of about 45C and at about 250-100 mbar pressure, about 90 g of solvent were distilled off to yield a concentrated residue containing the desired product.

The synthetic route of 148017-28-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GONG, Yong; ZINSER, Hartmut B.; WO2013/49021; (2013); A1;,
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Electric Literature of 1118-69-0, A common heterocyclic compound, 1118-69-0, name is N-Isopropylacetamide, molecular formula is C5H11NO, 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.

In a fashion similar to the preparation of 1, treatment of tetrakis(dimethylamido)hafnium (0.200 g, 0.563 mmol) with N-isopropylacetamide (0.228 g, 2.25 mmol) in refluxing toluene (15 mL) for 3 h afforded 6 as colorless crystals (0.219 g, 67%) upon sublimation at 105 C/0.05 Torr: mp 207-210 C; IR (Nujol, cm-1) 1579 (s), 1404 (s), 1365 (s), 1344 (s), 1319 (m), 1188 (s), 1170 (m), 1127 (m), 1053 (m), 988 (m), 887 (m), 823 (m), 816 (m), 618 (s), 584 (s); 1H NMR (C6D6, 23 C, delta) 3.47 (septet, J = 6.5 Hz, 4H, CH(CH3)2), 1.70 (s, 12H, CH3), 1.23 (d, J = 6.5 Hz, 24H, CH(CH3)2); 13C{1H} NMR (C6D6, 23 C, ppm) 182.44 (s, C=O), 48.67 (s, CH(CH3)2), 23.86 (s, CH(CH3)2), 17.37 (s, CH3). Anal. Calcd for C20H40HfN4O4: C, 41.48; H, 6.96; N, 9.68. Found: C, 41.32; H, 6.85; N, 9.77.

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; Karunarathne, Mahesh C.; Baumann, Joseph W.; Heeg, Mary Jane; Martin, Philip D.; Winter, Charles H.; Journal of Organometallic Chemistry; vol. 847; (2017); p. 204 – 212;,
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