Tag: M.W=300-400

224789-21-3, name is 2-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one, 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. Safety of 2-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

EXAMPLE 1 (procedure for the preparation of 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4- dihydroimidazo-[5,l-fJ[l,2,4]triazin-2-yl)benzenesulfonylchloride)A solution of 50 g of 2-(2-ethoxyphenyl)-5-methyl-7-propyl-3H-imidazo[5, l-f][l,2,4]triazin- 4-one, dissolved in 500 ml of dichloromethane was added dropwise to a solution of 100 ml of chlorosulfonic acid and 50 ml of dichloromethane during ca. 90 minutes. The mixture was further stirred at laboratory temperature (23 C) overnight, 24 hours in total. On the following day, the reaction mixture was poured into 800 g of ice. After the ice has thawed, the mixture was thoroughly mixed. The precipitated solid substance was filtered off, the filtration cake was washed with dichloromethane (2 x 100 ml) and the isolated solid product was vacuum dried (20 C, 1 to 2 kPa (10 to 20 mbar)). The product was obtained in the form of an off-white powder in the yields of from 1 10 to 1 15% (calculated on the non-protonated form of the product).

The synthetic route of 224789-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENTIVA, K.S.; HALAMA, Ales; STRELEC, Ivo; DAMMER, Ondrej; WO2013/75680; (2013); A1;,
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Synthetic Route of 316146-27-7, These common heterocyclic compound, 316146-27-7, name is N-(4-Bromophenyl)-3-phenylpropanamide, 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.

b) Preparation of intermediate 5; The reaction was carried out twice. POCl3 (1.225 mol) was added dropwise at 10¡ãC to DMF (0.525 mol). Then intermediate 4 (0.175 mol) was added at room temperature. The mixture was stirred overnight at 80¡ãC, poured out on ice and extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The product was used without further purification. Yield: 77.62 g of intermediate 5 (67 percent).

The synthetic route of 316146-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/14885; (2007); A1;,
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77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, 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. HPLC of Formula: C13H12N2O5S

To a solution of N-(benzyloxy)-2-nitrobenzenesulfonamide (212 g, 0.69 mol) in THF (1000 mL) was added (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate (171 g, 0.63 mol) and PPh3 (275 g, 1.05 mol), followed by dropwise addition of a solution of DEAD (195 g, 1.12 mol) in THF (500 mL). The mixture was then stirred at 20 C. overnight. The reaction mixture was then concentrated in vacuum and purified by silica gel column chromatography (3:1 petroleum ether/EtOAc) to afford (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (283.8 g, 80%) as a yellow oil

The synthetic route of 77925-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hwang, You Seok; Gu, Jian-Qiao; Jain, Akash; Garad, Sudhakar; Sizemore, Jacob P.; US2014/275001; (2014); A1;,
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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. 24310-36-9, name is 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydrobenzo[b]azepin-5-one, A new synthetic method of this compound is introduced below., Quality Control of 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydrobenzo[b]azepin-5-one

A solution of Br2 (558 mg, 3.48 mmol) in DCM (10 mL) was added dropwise to compound from Example 1 step 1 (1.00 g, 3.17 mmol), NBS (57 mg, 0.32 mmol), Et3N (352 mg, 3.48 mmol) in DCM (50 mL) at rt. The mixture was stirred at 50oC for 5 hrs and then quenched with water, extracted with DCM. The organic layer was washed with NaHCO3 (aq), concentrated and purified by silica gel column chromatography to give the desired compound (1.2 g, 96%) as brown solid. ESI MS m/z = 394.15 [M+1].

The synthetic route of 24310-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; YU, Jianming; SHOOK, Brian, C.; BLAISDELL, Thomas, P.; KIM, In, Jong; PANARESE, Joseph; MCGRATH, Kevin; NEGRETTI-ENMANUELLI, Solymar; OR, Yat, Sun; (301 pag.)WO2017/123884; (2017); A1;,
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Synthetic Route of 26638-53-9, A common heterocyclic compound, 26638-53-9, name is 3-Chloro-6,11-dihydro-6-methyl-5,5,11-trioxodibenzo[c,f][1,2]thiazepine, molecular formula is C14H10ClNO3S, 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.

N-bromosuccinimide (187 mg, 1.05 mmol) was added portionwise to a solution of ketone 3f (308 mg, 1.0 mmol) and FeCla (324 mg, 2.0 mmol) in CH2CI2 (10 mL) and CH3CN (5 mL) , and the reaction mixture was stirred at room temperature for 3 h. Additional W-bromosuccinimide (187 mg, 1.05 mmol) was then added and the reaction mixture was stirred at room temperature for a further 14 h. The reaction mixture was washed with water and brine and dried over NaSCli. The crude product was purified by column chromatography ( CH2CI2 : hexane – 2:1) followed by crystallization from MeOH. The product 3k was obtained as a white solid (290 mg, 75 percent) . XH NMR (400 MHz, Acetone-dg) 3 8.31 (d, J = 2.5 Hz, 1H) , 8.00 – 7.96 (m, 1H) , 7.95 – 7.89 (m, 3H) , 7.58 (d, J = 8.7 Hz, 1H) , 3.44 (s, 3H) ; 13C NMR (101 MHz, Acetone-dg) delta 189.6, 142.0, 139.1, 139.0, 138.4, 135.3, 134.7, 134.3, 132.8, 127.9, 125.8, 119.4, 39.3; LR-MS calcci. for C ,HioBrClN03S [M+H]+ 387.92, found 388.63.

The synthetic route of 26638-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; KRUEGEL, Andrew C.; HENKE, Adam; GASSAWAY, Madalee M.; RIVERS, Marie-laure; JAVITCH, Jonathan A.; SAMES, Dalibor; WO2015/138791; (2015); A1;,
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Electric Literature of 1032350-06-3, 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. 1032350-06-3, name is tert-Butyl (1-(4-bromophenyl)cyclobutyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

27.75 g (55 mmol) [1 -(4-Bromo-phenyl)-cyclobutyl]-carbamic acid tert-butyl ester,23.76 mmol (93.6 mmol) bis-(pinacolato)diboron, 25 g (255 mmol) potassium acetate and 2.08 g (2.55 mmol) 1 ,1 ‘-bis(diphenylphosphino)ferrocenedichloro- palladium(ll) in 500 mL degassed THF were heated for three hours at reflux. The colour of the reaction mixture turned from dark red to black. Due to an incomplete reaction heating was continued for another two hours. The reaction mixture was poured on water (400 mL) and diluted with ethyl acetate (700mL). After stirring for 30’ the organic phase was separated and the aqueous phase was reextracted twice with ethyl acetate (400 and 200 mL). The combined organic extracts were washed with brine (200 mL) and dried (sodium sulfate). After evaporation of the solvent the residue was purified by chromatography (Biotage) yielding 28.99 g (91 .3%) of the title compound.1 H NMR (400 MHz, d6-DMSO): delta 7.51 -7.67 (m, 3H), 7.38 (d, 2H), 2.22-2.42 (m, 4H), 1 .88-2.02 (m, 1 H), 1 .63-1 .80 (m, 1 H), 1 .00-1 .38 (m, 21 H) ppm.

The synthetic route of tert-Butyl (1-(4-bromophenyl)cyclobutyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; INCE, Stuart; HAEGEBARTH, Andrea; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; SCOTT, William; WO2012/7345; (2012); A2;,
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Electric Literature of 224789-21-3,Some common heterocyclic compound, 224789-21-3, name is 2-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one, molecular formula is C17H20N4O2, 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 15A 4-Ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride At 0 C., 2.00 g (6.4 mmol) of 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one are slowly added to 3.83 ml of chlorosulphonic acid. At room temperature, the reaction mixture is stirred ovemight, and then poured into ice-water and extracted with dichloromethane. This gives 2.40 g (91%) of a colourless foam. 200 MHz 1H-NMR (CDCl3): 1.03, t, 3H; 1.61, t, 2H; 1.92, hex, 2H; 2.67, s, 3H; 3.10, t, 2H; 4.42, quart., 2H; 7.27, t, 1H; 8.20, dd, 1H; 8.67, d, 1H; 10.18, s, 1H.

The synthetic route of 224789-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US6362178; (2002); B1;,
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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. 227940-71-8, name is tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

To a solution of 3 (350 mg, 1.11 mmol) in 30mL of dry ethanol was added 28 % of the Pd, 10 wt. % on activated carbon, and H2 was bubbled through the reaction mixture for 4 hrs. The reaction was monitored by TLC. The solution was filtered through a sintered funnel and evaporated to yield 230 mg of the product 4. Yield: 92 %. (HRMS): calcd for C12H23N2O2 m/z 227.1760, found m/z 227.1750

The synthetic route of 227940-71-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Haridas; Sadanandan, Sandhya; Sharma, Yogesh K.; Chinthalapalli, Srinivas; Shandilya, Ashutosh; Tetrahedron Letters; vol. 53; 6; (2012); p. 623 – 626;,
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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. 360773-84-8, name is tert-Butyl (1-(4-bromophenyl)cyclopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl (1-(4-bromophenyl)cyclopropyl)carbamate

General procedure: Compound 3a (1.42g, 4.73mmol) in a 3.0N HCl solution in MeOH (10mL) was stirred at rt for 24h. The solvent was removed under reduced pressure. The resulting residue was then suspended in DCM and basified by a 2.0N solution of NaOH (20mL). The organic phases were then separated and combined and dried by anhydrous magnesium sulfate. The solvent was then removed and the residue was purified by column chromatography with pre-packed silica gel disposable column to afford the title compound 1a (1.12g, 99%) as a brown foam.

According to the analysis of related databases, 360773-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Dehui; Zheng, Hongchao; Wang, Xiaodong; Tetrahedron; vol. 72; 16; (2016); p. 1941 – 1953;,
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Electric Literature of 200283-08-5, The chemical industry reduces the impact on the environment during synthesis 200283-08-5, name is tert-Butyl (2-((tert-butoxycarbonyl)amino)ethyl)(2-hydroxyethyl)carbamate, I believe this compound will play a more active role in future production and life.

General procedure: The corresponding Boc-protected aminoalcohol was dissolved in dry acetonitrile.N-methylisatoic anhydride and K2CO3 were added to the solution. The mixture was stirredfor 48 h at room temperature. The solvent then was removed by evaporation and the crudeproduct was purified by centrifugally accelerated, radial, thin-layer chromatography. Theeluent was changed from n-hexane to n-hexane/acetone to acetone. The fractions whichcontained the product (TLC) were combined and the solvent was removed by evaporation. 3a: For the synthesis of 3a, the following was used: 2a (2.94 g, 9.7 mmol), CH3CN (100 mL),N-methylisatoic anhydride (2.60 g, 14.7 mmol), K2CO3 (6.9 g, 50 mmol). Yield: 1.26 g (31%).White powder. 1H NMR (200 MHz, CDCl3), delta (ppm): 1.40 (s, 18H, 6CH3), 2.88 (s, 3H, CH3), 3.27(br, 2H, CH2), 3.38 (br, 2H, CH2), 3.55 (br, 2H, CH2), 4.32 (t, 3J(H/H) = 5.43 Hz, 2H, CH2), 6.54 (ddd,J(H/H) = 8.1, 7.2, 1.0 Hz, 1H, CArH), 6.63 (d, 3J(H/H) = 8.5 Hz, 1H, CArH), 7.35 (ddd, J(H/H) = 8.6,7.1, 1.7 Hz, 1H, CArH), 7.85 (dd, J(H/H) = 8.0, 1.6 Hz, 1H, CArH). 13C NMR (200 MHz, CDCl3), delta(ppm): 28.51 (s, CH3), 28.57 (s, CH3), 29.7 (s, CH3), 39.7 (s, CH2), 46.7 (s, CH2), 62.4 (s, CH2), 80.5(s, OC(CH3)3), 109.8 (s, CipsoCOO), 111.0 (s, CAr), 114.6 (s, CAr), 131.8 (s, CAr), 135.0 (s, CAr), 152.3(s, CipsoN), 156.1 (s, N(CO)O), 168.5 (s, (CO)O).

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, tert-Butyl (2-((tert-butoxycarbonyl)amino)ethyl)(2-hydroxyethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Walther, Till; Herzog, Renate; Kalu?erovi?, Milena R.; Wagner, Christoph; Schmidt, Harry; Kalu?erovi?, Goran N.; Journal of Coordination Chemistry; vol. 71; 2; (2018); p. 243 – 257;,
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