Tag: M.W=100-200

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. 1015-89-0, name is Phenanthridin-6(5H)-one, A new synthetic method of this compound is introduced below., SDS of cas: 1015-89-0

The 5,6-dihydro-phenanthridine (Ik) was prepared using the following procedure: Into a 500 mL round bottom flask equipped with a magnetic stir bar and a reflux condensor was placed 6(5H)-Phenanthridinone (1000 mg, 5123 mumol), THF (250 mL) (fine suspension). The flask is sparged with nitrogen, 2M BH3-dimethylsulfide complex in THF (10 mL) is added. This is allowed to stir at reflux for 24 hours. TLC shows reaction still incomplete (1/1, ethyl acetate/heptane). Solvents removed under reduced pressure. Water (50 mL) and ethyl acetate (100 mL) added. The aqueous layer is separated with ethyl acetate (3 x 100 mL). The organic layers are combined, dried(sodium sulfate), solids removed by filtration, and the solvents removed under reduced pressure. This is purified by silica column chromatography using heptane to 50percent ethylacetate in heptane. The best fractions are pooled and the solvents are removed under reduced pressure to afford an off-white solid (270 mg, Yield: 29percent). LC-MS shows mass 182 (M+H)+.

The synthetic route of 1015-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96001; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 116861-31-5, 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 116861-31-5 as follows.

Synthesis of compound 22: the aforementioned compound 20 (0.120 g, 0.00049 mol, 1 eq) was solubilised in DMF (3 ml). To the solution was added the aforementioned compound 21 (0.104 g, 0.00054 mol, 1.1 eq) solubilised in DMF (2 ml). The reaction mixture was stirred under reflux for 6 hours. The structure of the product was evaluated by TLC CH2Cl2 9/MeOH 1/NH4OHaq 33% 0.03. The solvent was evaporated, and the oily residue was purified by flash chromatography using a mixture of CH2Cl2 9/MeOH 1/NH4OHaq 33% 0.03 as the eluent phase. 0.084 mg of a yellow oil were obtained. Yield 42.71%. 1H NMR (400 MHz, CDCl3) delta 0.87 (d, 6H, J=6.8 Hz), 1.43 (s, 18H), 1.57-1.61 (m, 7H), 1.98-2.01 (m, 2H), 2.31-2.35 (m, 2H), 2.38-2.42 (m, 2H), 3.10-3.12 (m, 2H), 3.16-3.18 (m, 2H), 4.72 (brs, 1H, exch D2O), 5.69 (brs, 1H, D2O exch.).

According to the analysis of related databases, 116861-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Giuliani, Giammaria; Paus, Ralf; Benedusi, Anna; Marzani, Barbara; Baroni, Sergio; US2015/202132; (2015); 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. 1520-70-3, name is Ethanesulfonamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C2H7NO2S

Example 19: 5-(4-CHLOROPHENYL)-6-CYCLOHEXYL-N-(ETHYLSULFONYL)-4-(2- MORPHOLIN-4-YL-2-OXOETHYL)-4H-THIENO [3, 2-B] PYRROLE-2-CARBOXAMIDE; A solution (0.015 M) of 5- (4-CHLOROPHENYL)-6-CYCLOHEXYL-4- (2-MORPHOLIN-4- YL-2-OXOETHYL)-4H-THIENO [3, 2-B] PYRROLE-2-CARBOXYLIC acid in THF at RT was treated with CDI (1. 1 eq. ) and DMAP (1.1 eq. ). After stirring for 1H at RT, ETHANESULFONAMIDE (2 eq. ) and DBU (2 eq. ) were added. The mixture was heated to reflux for 5 h then cooled down and diluted with AcOEt. The organic phase was washed with aqueous HC1 (0.1 N) and dried. Evaporation of the solvent under reduced pressure gave a residue which was purified by RP-HPLC (Conditions : Waters X-TERRA MS C18,10 micron, 19 x 100 mm ; flow : 20 ML/MIN ; Gradient : A: H20 + 0.05percent TFA ; B : MECN + 0.05percent TFA ; 50percent A isocratic for 1 min then linear to 20percent A in 9 min) to afford the title compound (17percent) as a solid. ‘H NMR (400 MHz, DMSO-d6, 300 K) 8 1. 1-1.3 (m, 7H), 1.5-1. 8 (m, 8H), 2.44 (m, 1H), 3.4-3. 6 (m, 8H), 4.83 (s, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.61 (d, J = 8. 0 Hz, 2H), 8. 07 (s, 1H), 11.91 (bs, 1H); MS (ES+) M/Z 578, 580 (M+H) +.

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; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2005/23819; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 154350-29-5, 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 154350-29-5 as follows.

A mixture of 2-(3-fluoro-5-pyrrolidin-1-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (50 mg, 0.14 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (39 mg, 0.20 mmol), 4-dimethylaminopyridine (24.4 mg, 0.20 mmol), cyclopropanesulfonic acid amide (51 mg, 0.42 mmol) in dichloromethane (3 mL) was heated for 12 hours at 60° C. Removal of the solvent afforded an oil residue. Purification by Waters automated flash system (column: Xterra 30 mm.x.100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1percent formic acid in water) afforded cyclopropanesulfonic acid [2-(3-fluoro-5-pyrrolidin-1-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (13 mg, 20percent) as a light yellow solid: LC/MS m/e calcd for C25H30FN3O3S (M+H)+: 472.6, observed: 472.2.

According to the analysis of related databases, 154350-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chen, Li; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Wu, Jim Zhen; Zhou, Mingwei; US2011/257151; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 193751-54-1, 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 193751-54-1 as follows.

To a solution of N-l-Boc-amino-3-cyclopentene (1.94 g, 10.58 mmol) in a mixture of acetone (63 mL)/water (7.8 mL) (8: 1) at room temperature was added N-methyl morpholine N-oxide (2.48 g, 21.16 mmol). After 2 minutes osmium tetroxide (4% in water) (3.37 mL) was added and the resulting mixture stirred at room temperature for 23h. The reaction mixture was then quenched by the addition of aqueous Na2S203 (0.2 M, 25 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed with aqueous Na2S203 (0.2 M, 10 mL), dried (MgS04), filtered and evaporated in vacuo. The crude material was purified by flash chromatography eluting with EtOAc (17 – 100 %) in heptane to give a mixture of the title compounds as a yellow solid (1.31g, 57 %).

According to the analysis of related databases, 193751-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 154350-29-5, 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. 154350-29-5, name is Cyclopropanesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 7: Synthesis of (IS, 4R, 6S, 14S, 18R)- [7-cis-4-Cyclopropanesulfonylaminocarbonyl-12-cyclopropyl-18-(tert-butyldimethylsilyloxy)- 2, 15-dioxo-3, 12,16-triaza-tricyclo[14.3.0. (f’6]nonadec-7 -en-14-yl] carbamic acid, tert-butyl ester.; (15, AR, 65, 145, 18R)-7-c-14-tert-Butoxycarbonylamino-18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3, 12,16-triazatricyclo[ 14.3.0.04’6]nonadec-7-ene- 4-carboxylic acid (490 mg, 0.79 mmol) was dissolved in 15 mL of THF and treated with CDI (179 mg, 1.10 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere.) After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (134 mg, 1.10 mmoL) and DBU (168 mg, 1.10 mmoL). After stirring overnight at rt, the THF was removed by rotary evaporation. The residue was dissolved in water and IN HCl was added until the pH = 5. This aqueous solution was extracted with EtOAc (3x). The combined EtOAc extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash column, eluting with 3percent methanol in methylene chloride, gave 300 mg (53percent) Of (IS”, 4R, 65, 145, 18R)- [7-c-4-Cyclopropanesulfonylaminocarbonyl-12- cyclopropyl- 18-(tert-butyldimethylsilyloxy)-2, 15 -dioxo-3 ,12,16-triaza- tricyclo[14.3.0.04’6]nonadec-7-en-14-yl]carbamic acid, tert-butyl ester as a white solid: LC-MS (Phenomenex 10 mum Cl 8 HPLC column: 3.0×50 mm length. Gradient: 100percent Solvent A/0percent Solvent B to 0percent Solvent A/100percent Solvent B. Gradient time: 2 min. Hold time: 1 min. Flow rate: 5 mL/min. Detector Wavelength: 220 nM. Solvent A: 10percent MeOH / 90percent H2O / 0.1percent TFA. Solvent B: 10percent H2O / 90percent MeOH / 0.1percent TFA.) (Retention time: 2.40 min), MS m/z 724 (M++l).

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, Cyclopropanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64061; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 122334-37-6, 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. 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 2.2 6-(4-Chlorophenyl)-4-hydroxy-5-methyl-2H-pyran-2-one (IX) A suspension of 4.7 g of sodium hydride at 60% in oil, in 100 ml of THF, is cooled to 0 C. under a nitrogen atmosphere, a solution of 17 g of ethyl 3-oxopentanoate in 100 ml of THF is then added slowly, and the mixture is left to stir at 0 C. for 5 minutes. 86.5 ml of a 1.5 M solution of lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane is then added dropwise at 0 C., and the mixture is left to stir at 0 C. for 20 minutes. Finally, a solution of 23.5 g of the compound of Preparation 1.2 in 50 ml of THF is added slowly and the mixture is left to stir while allowing the temperature to return to AT, and stirred overnight at AT. A mixture of ice/HCl at 10% is added, the reaction mixture is extracted with EtOAc, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is taken up with 150 ml of concentrated H2SO4 and the mixture is left to stir at AT for 3 hours. The reaction mixture is poured onto ice and left to stir, and the precipitate formed is spin-filter-dried and washed with iso ether and then with pentane. 25 g of the expected compound are obtained after drying.

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, 4-Chloro-N-methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2009/281107; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 39549-79-6,Some common heterocyclic compound, 39549-79-6, name is 2-Amino-4-methylbenzamide, molecular formula is C8H10N2O, 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 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2molpercent), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120°C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2×5mL) and acetone (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

The synthetic route of 39549-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
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. 71510-95-7, name is Ethyl 3-(methylamino)-3-oxopropanoate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 3-(methylamino)-3-oxopropanoate

General procedure: In a round bottom flask, unsaturated aldehyde 2 (0.25 mmol, 1 equiv), amidomalonate 1 (0.3 mmol, 1.2 equiv), catalyst (0.05 mmol, 20% mol), and KOAc (0.3 mmol, 1.2 equiv) were added sequentially in 1 mL of 2,2,2-trifluoroethanol. The reaction was stirred at room temperature overnight. Then the crude was purified by column chromatography to furnish piperidine adducts 3.

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 71510-95-7.

Reference:
Article; ?ihalova, Sylva; Valero, Guillem; Schimer, Ji?i; Humpl, Marek; Dra?insky, Martin; Moyano, Albert; Rios, Ramon; Vesely, Jan; Tetrahedron; vol. 67; 46; (2011); p. 8942 – 8950;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6329-26-6, These common heterocyclic compound, 6329-26-6, name is Ethyl (2-chloroethyl)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.

a) A mixture of 1-(4-bromophenyl)piperazine (0.018 mol) and ethyl (2-chloroethyl)-carbamate (0.036 mol) was stirred for 2 hours at 130 C. Triethylamine (3 ml) was added and the mixture was stirred for 15 minutes at 130 C. The reaction mixture was cooled to room temperature, CH2 Cl2 was added and the resulting mixture was washed with water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3 OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 4.3 g (67.2%) of ethyl [2-[4-(4-bromophenyl)-1-piperazinyl]-ethyl]carbamate (interm. 1).

Statistics shows that Ethyl (2-chloroethyl)carbamate is playing an increasingly important role. we look forward to future research findings about 6329-26-6.

Reference:
Patent; Janssen Pharmaceutica, N.V.; US6103725; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics