Category: amides-buliding-blocks

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. 7700-07-4, name is N,N-Dimethylethenesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C4H9NO2S

(i) 2-(1H-Indol-5-yl)-N,N-dimethylethenesulphonamide A mixture of 5-bromoindole (7.7 g), N,N-dimethylethenesulphonamide (5.3 g) triethylamine (15 ml), acetonitrile (5 ml), palladium (II) acetate (0.35 g) and tri-o-tolylphosphine (0.95 g) was heated at 100 C. in an autoclave for 3 h. The resulting cooled mixture was partitioned between hydrochloric acid (2N, 300 ml) and ethyl acetate (2*150 ml). The combined extracts were dried (Na2 SO4) and evaporated in vacuo. The residue was purified by `flash` chromatography (V, 7 cm col.) to give the title compound as a crystalline solid (3.8 g) m.p. 148-150 C.

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; Glaxo Group Limited; US4994483; (1991); A;,
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Related Products of 5900-59-4, 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 5900-59-4 as follows.

General procedure: To an oven-dried 20 cm3 test tube with a ground-in stopperequipped with a stir bar were added anthranilamide (1.0 mmol), benzyl alcohol (1.0 mmol), KOH (2.0 mmol),and 4 cm3 toluene. The test tube was put in an oil bath potpreheated at 90 C and the mixture was stirred for 20 h at90 C. After cooling to room temperature, the reactionmixture was added about 5 g silica gel and directly condensedon a rotator under vacuum. The resulting residualwas transferred to a silica gel chromatography column andeluted with a solution of petroleum ether and ethyl acetate[4/1 (v/v)] to give a white solid 2-phenyl-4(3H)-quinazolinone.For some products (3f, 3g, 3n, and 3t) onlysparingly soluble in ethyl acetate, the reaction mixtureswere condensed in vacuo on a rotary evaporator. Theresiduals were washed three times with water and oncewith ethyl acetate, and then dried in an infrared oven togive the desired products pure enough for NMR analysis.

According to the analysis of related databases, 5900-59-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Qiu, Dezhi; Wang, Yanyan; Lu, Dongming; Zhou, Lihong; Zeng, Qingle; Monatshefte fur Chemie; vol. 146; 8; (2015); p. 1343 – 1347;,
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Electric Literature of 52898-49-4, A common heterocyclic compound, 52898-49-4, name is N,4-Dimethoxy-N-methylbenzamide, molecular formula is C10H13NO3, 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.

The preparation method is as follows:Ethylene glycol acetal (458 mg, 2 mmol) of 3-bromobenzaldehyde,Dissolved in 5 mL of dry tetrahydrofuran,N-Butyllithium (0.8 mL, 2 mmol) was slowly added dropwise at -70 C,After 1 hour, N-methyl-N-methoxy 4-methoxybenzamide (332 mg, 1.7 mmol) was added slowly at -70 C,The reaction was continued at -70 C for 2 hours,The reaction was quenched by adding 5 mL saturated brine and the organic phase was extracted with ethyl acetate (10 mL * 3)The combined organic phase,Drying over anhydrous sodium sulfate. Spin the solvent,Column chromatography (petroleum ether: ethyl acetate = 20: 1 as eluant),The reaction product 386mg.The reaction product was dissolved in 5 mL of dry methanol,1mL 6N hydrochloric acid was added at room temperature, the reaction for 1 hour,The reaction was quenched by addition of saturated sodium bicarbonate solution,The organic phase was extracted with ethyl acetate (10 mL * 3), the organic phases were combined,Drying over anhydrous sodium sulfate. Spin the solvent,Column chromatography (petroleum ether: ethyl acetate = 20: 1 as eluant),The reaction product of 3- (4-methoxybenzoyl) formylbenzaldehyde 294mg, 72% yield in two steps.

The synthetic route of 52898-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Li Wenbao; Sun Tianwen; Wang Shixiao; Zhao Jianchun; Hou Yingwei; Guan Huashi; (16 pag.)CN107286137; (2017); A;,
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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. 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (cis-3-hydroxycyclobutyl)carbamate

MsCl (5.386 g, 46.83 mmol, 2.00 eq.) was added dropwise to a cold solution of tert-butyl N-[trans-3- hydroxycyclobutyl] carbamate (4.379 g, 23.39 mmol, 1.00 eq.) and TEA (7.095 g, 70.12 mmol, 3.00 eq.) in dichloromethane (25 mL at 0C. The resulting solution was stirred for 3 hours at room temperature and it was then diluted with 200 mL of dichloromethane. The resulting mixture was washed with water (2×100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was recrystallized from dichloromethane/hexane in the ratio of 1 : 1 to give 5.548 g (89%) of tert-butyl N-[cis-3- (methanesulfonyloxy)cyclobutyl] carbamate as an off-white solid.

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; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
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Synthetic Route of 880166-10-9,Some common heterocyclic compound, 880166-10-9, name is Methyl 1-((tert-butoxycarbonyl)amino)cyclobutanecarboxylate, molecular formula is C11H19NO4, 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.

To a stirred suspension of LiAlH4(1.8 g, 46.4 mmol) in dry THF (15 ml), was slowly added a solution of methyl l-((tert-butoxycarbonyl)amino)cyclobutane-l-carboxylate (step 1, 5.32g, 23.2 mmol) in THF (15 ml) at 0 C. The reaction mixture was brought to room temperature and stirred for about 3 hours. After completion of the reaction (monitored by TLC), the reaction mixture was quenched by the sequential addition of 1.8 mL of H20, 5.4 mL of 15% aq. NaOH and 5.4 mL of H20. The mixture was then poured into EtOAc (100 ml) and stirred for about 30 minutes. The reaction mixture was filtered through celite, dried over Na2S04and concentrated under reduced pressure. The product was isolated by flash column chromatography on silica gel using (EtOAc: hexane-70:30) to give the desired product (3.7 g, yield: 80%) as an oil. 1H NMR (300 MHz, DMSO-d6): delta 6.62 (s, 1H), 4.67 (t, J = 5.4 Hz, 1H), 3.41 (d, J = 5.4 Hz, 2H), 2.22-2.09 (m, 2H), 2.01-1.90 (m, 2H), 1.65-1.57 (m, 2H), 1.36 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-((tert-butoxycarbonyl)amino)cyclobutanecarboxylate, its application will become more common.

Reference:
Patent; HETERO RESEARCH FOUNDATION; BANDI, Parthasaradhi Reddy; KURA, Rathnakar Reddy; ADULLA, Panduranga Reddy; GAZULA LEVI, David Krupadanam; MUKKERA, Venkati; NEELA, Sudhakar; LANKA, Vl Subrahmanyam; (170 pag.)WO2017/17630; (2017); A1;,
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Synthetic Route of 123986-64-1, 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. 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 281,1-Dimethylethyl [(4-{[3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate; A solution of 5-chloro-N-[(5-chloro-2-thienyl)sulfonyl]-N-[4-(methyloxy)-1 H-indazol-3-yl]-2-thiophenesulfonamide (for a preparation see Intermediate 10)(400 mg, 0.763 mmol), triphenylphosphine (400 mg, 1.52 mmol) and 1,1-dimethylethyl{[4-(hydroxymethyl)phenyl]methyl}carbamate (Maybridge) (362 mg, 1.52 mmol) in THF (3 mL) was added at room temperature DIAD (0.300 mL, 1.52 mmol). The resulting mixture was stirred at 65 C. for 3 hours. The reaction mixture was partitioned between DCM (3 mL) and water (3 mL). The organic phase was separated, and the aqueous layer was further extracted with DCM (3 mL). The combined organic solutions were dried over an hydrophobic frit and evaporated under a nitrogen stream in a blowdown unit. The residue was loaded in dichloromethane on a silica (50 g) cartridge and purified by chromatography on Flashmaster II using a gradient of 0-100% dichloromethane-cyclohexane over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound (498 mg, 88%) as a gum.LCMS (System A) RT=1.48 min, ES+ve m/z 760/762 (M+NH4)+.

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

Reference:
Patent; Hodgson, Simon Teanby; Lacroix, Yannick Maurice; Procopiou, Pauayiotis Alexandron; US2010/216860; (2010); A1;,
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111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)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. Safety of tert-Butyl (trans-4-hydroxycyclohexyl)carbamate

(1) To a solution of tert-butyl(trans-4-hydroxycyclohexyl)carbamate (1.08 g, 5.00 mmol) and 15-crown 5 (1.04 mL, 5.25 mmol) in tetrahydrofuran was added sodium hydride (60% dispersion in mineral oil, 440 mg, 11.0 mmol) at 0 C., followed by iodomethane (0.327 mL, 5.25 mmol) at 0 C. After being stirred for 2 hour, the reaction mixture was poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, died over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography to give tert-butyl(trans-4-methoxycyclohexyl)carbamate as a colorless solid (796 mg, 69%). MS (APCI): m/z 247 (M+NH4), 230 (M+H).

The synthetic route of 111300-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1129-26-6, name is 4-Methoxybenzenesulfonamide, belongs to amides-buliding-blocks compound, 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 1129-26-6, Application In Synthesis of 4-Methoxybenzenesulfonamide

To p-methoxybenzenesulfonamide (5.00 g, 26.7 mmol, 1.00 equiv) in methanol (100 mL) at 23 C was added potassium hydroxide (3.75 g, 66.8 mmol, 2.50 equiv). The reaction mixture was stirred at 23 C for 10 min and subsequently cooled to 0 C. To the reaction mixture at 0 C was added iodobenzene diacetate (8.60 g, 26.7 mmol, 1.00 equiv). The reaction mixture was stirred at 0 C for 10 min and further stirred at 23 C for 2.0 h. The reaction mixture was poured into cold water (700 mL) and kept at 0 C for 4 h. The suspension was filtered off and the filter cake was washed with water (2 x 200 mL) and methanol (2 x 200 mL) to afford 7.90 g of the title compound as a colorless solid (76% yield).NMR Spectroscopy: NMR (500 MHz, DMSO-cfe, 23 C, delta): 7.70 (d, J = 7.5 Hz, 2H), 7.49-7.44 (m, 3H), 7.32-7.28 (m, 2H), 6.78 (d, J = 8.5 Hz, 2H), 3.74 (s, 3H). 13C NMR (125 MHz, DMSO- , 23 C, delta): 160.6, 136.9, 133.2, 130.5, 130.2, 128.0, 117.0, 113.4, 55.4. These spectroscopic data correspond to the reported data in reference8.

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-Methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; LEE, Eunsung; KAMLET, Adam, Seth; POWERS, David; FURUYA, Takeru; WO2012/24604; (2012); A2;,
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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. 597563-17-2, name is tert-Butyl (1-(3-bromophenyl)cyclopropyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 597563-17-2

Step 2. [1-(3-Pyrazol-1-yl-phenyl)-cycIopropyl]-carbamic acid tert-butyl ester (4).This was prepared according to the literature: Antiila, J. C. et al. J. Org. Chem. 2004, 69, 5578-5587. A mixture of 1.49 g (4.8 mmol, 1.0 eq) of 1 , 0.49 g (7.2 mmol, 1.5 eq) of 2, and 1.61 g (11.7 mmol, 2.4 eq) of K2CO3 in 6.5 mL of dry toluene was prepared. While stirring, 0.15 mL (0.95 mmol, 0.20 eq) of 3 and 0.10 g (0.52 mmol, 0.11 eq) of CuI was added. The mixture was purged with N2 and was heated in a sealed vessel at 110 C for 20 h. After cooling to room temperature, the crude reaction mixture was flash chromatographed on silica with a step gradient of 20% and 30% EtOAc/hexanes as eluents. After concentration by rotary evaporation, 0.70 g (49% yield) of viscous yellow oil was isolated as product 4. (M + H)+ = 300.2. 1H-NMR (CDCI3) delta 7.92 (m, 1 H), 7.73 (m, 1 H), 7.60 (s, 1 H), 7.51 (d, J = 8.1 Hz, 1 H), 7.39 (m, 1 H), 7.18 (d, J= 7.8 Hz, 1 H), 6.48 (s, 1 H), 1.46 (s, 9H), 1.28 (m, 4H).

The synthetic route of 597563-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2007/47306; (2007); A1;,
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Reference of 122848-57-1,Some common heterocyclic compound, 122848-57-1, name is tert-Butyl 3,6-diazabicyclo[3.2.0]heptane-6-carboxylate, molecular formula is C10H18N2O2, 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.

To a 10 mL microwave reaction vessel compound 5-chloro-6-ethyl-2- (pyrido[3,2-b]pyrazin-7-ylthio)-7H-pyrrolo[2,3-d]pyrimidin-4-yl 4-methylbenzenesulfonate (Example 19) (0.02 g, 0.039 mmol) and tert-butyl 3,6-diazabicyclo[3.2.0]heptane-6- carboxylate (7.7 mg, 0.039 mmol) was dissolved in ethanol (0.1 mL). The reaction was sealed and heated to 100C for 0.5 h after which the solvent was removed and the crude was used for the next step without further purification

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 3,6-diazabicyclo[3.2.0]heptane-6-carboxylate, its application will become more common.

Reference:
Patent; TRIUS THERAPEUTICS, INC.; CREIGHTON, Chris; TARI, Les; CHEN, Zhiyong; HILGERS, Mark; LAM, Thanh; LI, Xiaoming; TRZOSS, Michael; ZHANG, Junhu; FINN, John; WO2011/32050; (2011); A2;,
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