Tag: M.W=200-300

Synthetic Route of 104060-23-3, A common heterocyclic compound, 104060-23-3, name is N-Boc-2-(4-Aminophenyl)ethanol, molecular formula is C13H19NO3, 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.

Compound 11A (2.5 g, 10.5 mmol, 1.00 equiv) was dissolved in 25 mL of DCM then cooled to -78C. A Dess-Martin Periodinane solution (DMP, 6.71 g, 15.8 mmol, 1.5 equiv) in DCM (10 mL) was added drop-wise. The cold bath was removed and agitation continued for 1 hour at ambient temperature. The reaction was neutralised with60 mL of a 50/50 mixture of sodium bicarbonate-saturated aqueous solution and Na2S2O3-saturated aqueous solution. The resulting solution was extracted 3 times with 30 mL of EtOAc. The organic phases were combined, washed twice with NaC1- saturated aqueous solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel (EtOAc/PE1/15) to yield 1.0 g (40 %) of compound 11B in the form of a pale yellow solid.

The synthetic route of 104060-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 1172623-95-8,Some common heterocyclic compound, 1172623-95-8, name is tert-Butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, molecular formula is C12H20N2O4, 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 N2 protection, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 ml), cooledto -10C or lower in an ice salt bath, and a solution of isopropyl magnesium chloride/lithium chloride in tetrahydrofuran(66 ml, 1.3 mol/l) was added dropwise, followed by stirring at about -10C for 1 hour. 1D (10 g, 39 mmol) was dissolvedin dry tetrahydrofuran (100 ml), and added dropwise to the reaction solution while the temperature was maintained at-10C. When the addition was complete, the reaction was allowed to proceed at room temperature for 4 hours. Thetemperature was lowered to about -10C, and a saturated ammonium chloride solution (40 ml) was added dropwise,followed by stirring for 10 min. The pH was adjusted to 5 to 6 with a 3 mol/l hydrochloric acid solution, to allow settlingand partitioning. The aqueous phase was extracted with methyl t-butyl ether (50 ml32). The organic phases werecombined, washed with a saturated sodium chloride solution (30 ml32), dried by addition of anhydrous sodium sulfatethereto, filtered, concentrated, and separated by column chromatography (petroleum ether/ethyl acetate (v/v) = 50:1 to8:1), to obtain a light yellow solid 1E (10.1 g, yield 83.5%).MS m/z (ESI): 210.1 [M-99].

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 (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, its application will become more common.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 456-64-4, 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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a-78 C solution of Preparation 30 (7.0 g, 19.1 mmol) in THF (80 mL) add potassium hexamethyldisilane (KHMDS) (53 mL, 0.5 M solution in toluene, 26.7 mmol) over 5 min. Add hexamethylphosphoramide (HMPA) (4.64 mL, 26.7 mmol) quickly, and stir the solution at-78 C for 25 min. Add a solution of N-phenyl triflamide (11.5 g, 32.2 mmol) in THF (15 mL + rinse) via syringe. Maintain the resulting solution at-78 C for 2 h, then pour the reaction contents into 1/2 SATD. NAHCO3 AND extract with ET20 (150 ML) and EtOAc (2 x 75 mL). Wash the combined organic extracts with H2O (2 x 100 mL) and brine (100 mL), dry over NA2SO4, and concentrate. Purification of the crude product by MPLC (0 to 12 to 25% EtOAc/hexanes) affords Preparation 31 (6.25 g, 66%) as an OFF-WHITE SOLID. H NMR (CDC13) 8 7.25-7. 43 (m, 5 H), 6. 84 (d, J = 8.8 Hz, 1 H), 6. 80 (dd, J = 8.8, 2.8 Hz, 1 H), 6.72 (d, J = 2. 8 Hz, 1 H), 5.02 (s, 2 H), 4.04 (m, 4 H), 3. 82 (dd, J = 4.4, 12. 8 Hz, 1 H), 2.66 (dq, J = 14.0, 2.4 Hz, 1 H), 2.21 (m, 2 H), 1.91 (m, 1 H), 1. 80 (t, J = 12.8 Hz, 1 H), 1.64 (TD, J = 12.8, 4.4 Hz, 1 H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/94400; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 25216-74-4, name is tert-Butyl (3-bromophenyl)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. Application In Synthesis of tert-Butyl (3-bromophenyl)carbamate

19 g (475 mmol) of sodium hydride (60% in oil) are added.in small amounts to a solution of 114 g (447 mmol) of tert-butyl (3-bromobenzyl) carbamate in 800 ml of dimethylformamide and the reaction medium is stirred until evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is maintained for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated by settling, dried over magnesium sulphate and evaporated. 115 g of tert-butyl (3-bromobenzyl)-N-methylcarbamate are obtained. Yield = 95%.

The synthetic route of tert-Butyl (3-bromophenyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2005/108352; (2005); 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. 195314-59-1, name is tert-Butyl (4-aminocyclohexyl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 195314-59-1

To a cooled (0C) solution of cyanuric chloride (1 eq.) in THF and DIPEA is added dropwise, (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (2 eq.) in THF. After stirring at RT for 1 hour, the solvent is removed in vacuo and the product is partitioned between DCM and 2 M HCl. The organic portion is separated, washed with water, brine, dried (MgSO4) and concentrated in vacuo to yield Intermediate IAl which is used in the next step without further purification.

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/121924; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 35303-76-5 as follows. Safety of 4-(2-Aminoethyl)benzenesulfonamide

DCE (20 mL) in 4- (2-aminoethyl)benzenesulfonamide(110mg, 0.55mmol), AcOH (0.10mL) and tert- butyl 2- (2-formyl -1H-imidazol-1-yl) acetic acid (250mg, 1.19mml) a solution containing the mixturewas stirred for 30 minutes at 80 under nitrogen. The reaction mixture was cooled to 0 , and treated with NaBH (OAc) 3 (3.165g,15mmol). The reaction mixture was stirred at room temperature overnight anddecomposed with water. The reaction mixture was extracted with DCM. The organiclayer was dried and concentrated in vacuo. The residue was purified by flashchromatography on silica gel, tert-butyl 2,2 ‘- (2,2’ – (4-sulfamoyl-phenethylaza screw-yl) bis (methylene) bis (lH-imidazole-2,1 diyl)) resulted diacetate(132mg, 41percent).

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MOLECULAR INSIGHT PHARMACEUTICALS INCORPORATED; BABICH, JOHN W; (133 pag.)JP5856247; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 49690-09-7, 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. 49690-09-7 name is N-tert-Butyl 4-Nitrophenylsulfonamide, 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: Method b: To a solution of nitroarene (1.0 equiv.) in EtOH or MeOH (deoxygenated with bubbled Argon) was added Pd/C (10%) and hydrazine monohydrate 65% (3.0 equiv.) under Argon. The solution was stirred and heated at reflux for the indicated time. The reaction mixture was filtered over Celite, and the filtrate concentrated under reduced pressure.

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

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

46460-73-5, name is Benzyl (3-aminopropyl)carbamate, 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. Recommanded Product: Benzyl (3-aminopropyl)carbamate

To a solution of 1-methylethyl 2, 4-dichloropyrimidine-5-carboxylate (4.7 G) and ethyldiisopropylamine (3.4 ml) in ACETONITRILE (250 ML) phenylmethyl [3- AMINOPROPYL] CARBAMATE (4.2 g) was added at 0¡ãC. Subsequently the reaction mixture was stirred over night at room temperature. After evaporation the residue was chromatographed on SILICA GEL (DICHLOROMETHANE/ISOPROPANOL) to yield the title compound (5.9 G). ESI-MS : 407 and 409 (M+)

The synthetic route of 46460-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/48343; (2004); 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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., Product Details of 24036-52-0

To a 25 mL flask was added 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (0.46 g, 2 mmol), P2S5 (0.89 g, 4 mmol) and THF (8 mL), thereaction mixture was heated at 90 C and stirred for 8 h. After the reactionwas completed, the THF was removed at reduced pressure andpour into water, filtered dry and directly reacted with piperazine(0.34 g, 4 mmol) at 90 C in THF without purification. Then the THFwas removed at reduced pressure and the residue was purified on silicagel with chloroform/methanol (V:V 10:1) to give the title compound asa white powder. Yield 56.2%, oil. 1H NMR (400 MHz, DMSO-d6) delta 6.99(d, J=2.4 Hz, 1H, Ar-H), 6.92 (dd, J=8.4, 2.4 Hz, 1H, Ar-H), 6.74 (d,J=8.4 Hz, 1H, Ar-H), 4.76 (s, 2H, Ar-H), 3.50-3.39 (m, 4H, CH2¡Á2),3.19 (m, 4H, CH2¡Á2). ESI-MS: m/z 296.0 [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:
Article; Dong, Fu-Dan; Liu, Dan-Dan; Deng, Cheng-Long; Qin, Xiao-chun; Chen, Kai; Wang, Jian; Song, Hong-Rui; Ding, Huai-Wei; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3982 – 3991;,
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. 16091-26-2, name is 3′-Aminobenzanilide, A new synthetic method of this compound is introduced below., Recommanded Product: 3′-Aminobenzanilide

General procedure: Compound (1a-e) (1 eq.) and compound (2a-e) (1 eq.) were suspendedin 5 mL of glacial acetic acid. The suspension dissolved completely uponheating. The reaction was refluxed for 15-30 min. After completion ofreaction (as monitored by TLC), reaction mixture was allowed tocooled, and then 10 mL of water was added. The resulting precipitatewas then filtered and was washed with water, cold ethanol, and hexanesto give the product.25N-(3-(2-methyl-4-oxoquinazolin-3(4H)-yl)phenyl) benzamide (4a):TLC carried out in Hexane: Ethyl acetate (60:40) Rf=0.13; cream colorsolid (70%); M.P: 248-249 C; IR: 3290 cm-1 (NeH stretch),1658 cm-1 (C]O amide); HRMS: m/z calcd for C22H17N3O2: 355.39[M+H]+; found: 356.1565.

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; Qureshi, Shahnawaz I.; Chaudhari, Hemchandra K.; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2676 – 2688;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics