Amides-buliding-blocks

Application of 5466-88-6,Some common heterocyclic compound, 5466-88-6, name is 2H-1,4-Benzoxazin-3(4H)-one, molecular formula is C8H7NO2, 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 solution of 4H-Benzo[1,4]oxazin-3-one (2.5 g, 16.77 mmol) in DMF (10 mL) was added potassium tert-butoxide (2.81 g, 25.16 mmol) at 0 C. After stirring for 5 min, methyl iodide (3.54 g, 25.16 mmol) was added and the reaction mixture was stirred for another 3h. The reaction was quenched by addition of water and extracted with ethyl acetate (30 x 2 mL). The organic layer was washed with water (20 mL), and evaporated to get a crude product 2.2 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2H-1,4-Benzoxazin-3(4H)-one, its application will become more common.

Reference:
Patent; NOVARTIS AG; BEBERNITZ, Gregory, Raymond; BOCK, Mark, G.; REDDY, Dumbala Srinivas; HAJARE, Atul Kashinath; VYAVAHARE, Vinod; BHOSALE, Sandeep Bhausaheb; KURHADE, Suresh Eknath; SALUNKHE, Videsh; SHAIKH, Nadim, S.; BHUNIYA, Debnath; PALLE, P., Venkata; FENG, Lili; LIANG, Jessica; WO2011/48112; (2011); A1;,
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Reference of 6919-61-5, A common heterocyclic compound, 6919-61-5, name is N-Methoxy-N-methylbenzamide, molecular formula is C9H11NO2, 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.

To a solution of 5.0g (25.4 mmol) of tetaut-butyldimethyl-pent-4-ynylochiy-silane (prepared by the method of Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885-888) in 10OmL of THF at -78C under an atmosphere of N2 was added dropwise 10.2 mL (25.4 mmol) of 2.5 M nBuLi in hexane. After stirring for Ih at that temperature, 4.0 g (24.2 mmol) of N-methoxy-N-methyl benzamide (2-1) in 20 mL of THF was added, the cooling bath was removed, and stirring was continued for 3h at room temperature. The reaction was quenched with saturated aqueous NH4Cl, extracted with 2 x EtOAc, washed with brine, dried over Na2SO4, and concentrated. The crude material was loaded onto a 4Og silica gel cartridge and eluted with a gradient of 0 to 55% EtOAc in hexanes over 25 minutes to provide 6.3g (20.9 mmol, 87%) of the propargylic ketone (2-2) as a pale yellow oil. To a suspension of 2.2g (10.7 mmol) of CuBrOMS in 30 mL of THF at -78C was added 10.7 mL (21.4 mmol) of a 2.0 M solution of PhLi in dibutylether. After stirring for 1.5h, 2.7g (8.9 mmol) of the above prepared ketone 2-2 in 5mL of THF was added, and the mixture was allowed to stir for an additional 3h at -78C, and warmed to 00C for 15 minutes before being quenched with saturated aqueous NH4Cl. The mixture was partitioned with EtOAc, the layers were separated, the aqueous was extracted with 2 x EtOAc, the organics were combined, washed with brine, dried over Na2SO4, and concentrated. The crude material was loaded onto a 4Og silica gel cartridge and eluted with a gradient of 0 to 25% EtOAc in hexanes to provide 2.89g (7.6 mmol, 85%) of 2-3 as a yellow oil; NMR analysis indicated that there was a 1.1:1 mixture of E:Z isomers. Careful separation of a fraction of this material provided the pure isomers, whose identities were determined by ID NOE analysis. Data for 2-3-(E) (first to elute): 1HNMR (500 MHz, CDCl3) delta 8.0 (m, 2H), 7.6 – 7.4 (m, 8H), 7.1 (s, IH), 3.7 (t, J = 6.3 Hz, 2H), 3.1 (m, 2H), 1.75 (m, 2H), 0.9 (s, 9H), 0.01 (s, 6H) ppm. Data for 2-3-(Z) (second to elute): 1HNMR (500 MHz, CDCl3) delta 7.8 (m, 2H) 7.45 (m, IH), 7.35 (m, 2H), 7.25 – 7.1 (m, 5H), 6.7 (s, IH), 3.65 (t, J = 6.3 Hz, 2H), 2.65 (t, J = 7.6 Hz, 2H), 1.7 (m, 2H), 0.9 (s, 9H), 0.05 (s, 6H) ppm. Data for mixture 2-3: HRMS (ES) calc’d M + H for C24H32O2Si: 381.2245. Found: 381.2251

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; MERCK & CO., INC.; WO2006/7501; (2006); A2;,
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Electric Literature 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.

A -78 0C solution of 3-iodo-l -(6-methyl-pyridin-2-ylmethyl)-l H-quinolin-4-one (113 mg, 0.3 mmol, 1 equiv) in 3 mL of THF was treated with 1.65 mL of isopropyl magnesium chloride (1.1 equiv) for 2 hours. Then 4-chloro-N-methoxy-N-methyl- benzamide (46 muL, 1.2 equiv) was added and stirring continued at rt for 2 hours. The reaction was quenched by slow addition of saturated aqueous solution OfNH4Cl. Standard workup followed by HPLC purification gave 3-(4-chloro-benzoyl)-l-(6-methyl-pyridin-2-ylmethyl)- 1 H-quinolin-4-one. LCMS (ES) M+H 389.1

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; CHEMOCENTRYX, INC.; WO2007/59108; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 98-64-6, name is 4-Chlorobenzenesulfonamide, 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 98-64-6, Application In Synthesis of 4-Chlorobenzenesulfonamide

General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 °C, and acidified to pH 1 with addition of HCl aqueous solution (10percent), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 .x. 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (9a-16e) (Scheme 1).

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

Reference:
Article; Luo, Yin; Qiu, Ke-Ming; Lu, Xiang; Liu, Kai; Fu, Jie; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4730 – 4738;,
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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. 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11NO5S

(4) Add 245 g (1.0 mol) of methyl 2-methoxy-5-sulfamoylbenzoate prepared in step (3) and 2772 g of 5% sodium hydroxide solution by weight to the reactor, Stir the reaction for 20 h, and the reaction temperature does not exceed 40 . After the reaction, adjust the pH to 1 with 5% by weight of dilute hydrochloric acid and filter. The resulting filter cake is washed with water, dried, and recrystallized from methanol to produce 209.06 g of 2-methoxy-5-sulfamoylbenzoic acid, yield 90.5%.

According to the analysis of related databases, 33045-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suzhou Chenghe Pharmaceutical And Chemical Co., Ltd.; Chen Xiaoqiang; Fang Huan; (7 pag.)CN111100042; (2020); A;,
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Synthetic Route of 7150-72-3, The chemical industry reduces the impact on the environment during synthesis 7150-72-3, name is tert-Butyl vinylcarbamate, I believe this compound will play a more active role in future production and life.

General procedure: A 25 mL round bottom flask or 20 mL glass vial with a stir bar was charged with thiol (1.2 mmol) and enecarbamate or enamide (1.0 mmol) followed by the addition of water (5 mL, 0.2M). The reactions were stirred vigorously at room temperature for 18 hours. The aqueous reaction was extracted with EtOAc (3 x 20 mL). The organic layers were collected and dried with Na2SO4, filtered and the solvent evaporated to provide the crude product. The crude product was purified by column chromatography using hexanes/EtOAc in an increasing polarity up to 1:1 mixture. The fractions containing the desired product were concentrated to provide the desired thioethers.

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

Reference:
Article; Barman, Eliezer; Hourezadeh; Lim, Daniel; Tetrahedron Letters; vol. 60; 34; (2019);,
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Application of 4943-86-6, These common heterocyclic compound, 4943-86-6, name is 2-Amino-N-(4-chlorophenyl)benzamide, 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 solution of the substituted benzamide (1equiv) and ortho-bromobenzaldehyde(1.41 mmol, 1 equiv) in acetonitrile (5mL) was treated with cyanuric chloride(0.022 mmol, 10 mole %). The reaction mixture was stirred at room temperature for 5-10 min and formed precipitate was filtered and recrystallised with ethanol to obtain the compounds 1, 6a, 6b and 16.

Statistics shows that 2-Amino-N-(4-chlorophenyl)benzamide is playing an increasingly important role. we look forward to future research findings about 4943-86-6.

Reference:
Article; Sharma, Moni; Mahar, Rohit; Shukla, Sanjeev K.; Kant, Ruchir; Chauhan, Prem M.S.; Tetrahedron Letters; vol. 54; 46; (2013); p. 6171 – 6177;,
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Application of 6973-09-7, A common heterocyclic compound, 6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, molecular formula is C7H10N2O2S, 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.

To a stirred suspension of the product of Intermediate Example 4 (1.1 g, 3.7 mmol) in 10 mL of THF, was added 5-amino-2-methylbenzenesulfonamide (0.70 g, 3.8 mmol, 1.0 equiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (18 muL, 0.072 mmol) was added in one portion. After 5 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 16 mL of THF and dried in the air to yield 1.6 g (92%) of 5-({4- [(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methylbenzene sulfonamide monohydrochloride as a light yellow solid.

The synthetic route of 6973-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/64753; (2007); A2;,
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Related Products of 2895-21-8, 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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-{[6-(3-chlorophenyl)-4-oxo-4,5-dihydropyrazolo[1 ,5-a]pyrazin-2-yl]oxy}butyl acetate (0.25 g, P23) and potassium carbonate (0.18 g) in dry acetonitrile (6 ml.) 2-chloro- N-(1-methylethyl)acetamide (0.1 g) was added and the reaction was stirred at 8O0C on. After cooling the mixture was diluted with AcOEt and washed with chilly water and brine. The organic phase was dried, filtered and the solvent evaporated under vacuum. The crude was dissolved in THF (20 ml_), lithium hydroxyde (5 ml_, 0.5 M solution in water) was added and the mixture was stirred at RT for 2h. Solvent was removed under reduced pressure; the residue was taken up with AcOEt and washed with water. The organic phase was dried, filtered and evaporated under vacuum to give a mixture of the title compounds (0.21 g) that was used in next step without further purification.MS ( m/z): 433 [MH]+.

The chemical industry reduces the impact on the environment during synthesis N-Isopropyl-2-chloroacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/130232; (2009); A1;,
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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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., 57561-39-4

A 100 mL round-bottomed flask (rbf) equipped with a magnetic stirbar was charged withTHF (15 mL), water (15 mL) and 2-(methylamino)ethanol (2.00 mL, 25.0 mmol). To thestirred solution exposed to air Boc2O (5.9 g, 27 mmol) was added in 4 portions within 10min resulting in gas evolution. Several drops of sat. aq. NaHCO3 were added 40 min laterto keep the pH around 8. Most of THF was removed on a rotary evaporator 4.5 h after theBoc2O addition. The residue was transferred into a separatory funnel using EtOAc,washed with aq. 2.5 M NH4Cl (20 mL) and brine. The organic phase was dried overMgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporator.Using hexane transferred the crude product into a pre-weighed 100 mL rbf, removedvolatiles on the rotary evaporator (20 mm Hg). N-Methyl-N-Boc-aminoethanol wasobtained as colorless oil: 4.26 g (97%). A 3-neck rbf equipped with a magnetic stirbar, arubber septum, a glass stopcock (Teflon tape, central neck) and connected to a vacuumline was charged with 4.26 g of the protected amine (24.3 mmol). After evacuation andrefill with nitrogen 90 mL of THF freshly distilled from sodium-benzophenone ketyl wasadded. The flask was placed in an ice-water bath. Approx. 25 min later quickly added1.09 g of 60% NaH (27.2 mmol) in paraffin via the central neck. Approx. 20 min lateradded allyl bromide (2.15 mL, 24.8 mmol) with a syringe via the rubber septum followedby 0.4487 g of tetrabutylammonium iodide (1.21 mmol, 5 mol%) via the central neck.Approx. 2.5 h later removed the cold bath and let the reaction mixture stirring for 16 hunder nitrogen. The flask was immersed in ice-water bath followed by careful addition ofwater (20 mL, audible sound). The mixture was transferred into a 250 mL separatoryfunnel followed by addition of EtOAc (50 mL) and extraction. The organic phase was setaside and the aqueous phase was extracted with fresh portion of EtOAc (40 mL). Theorganic phases were combined, washed with aq. 2.5 M NH4Cl (50 mL) and brine, driedover MgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporatorleaving behind yellow oil, which was chromatographed on silica (normal phase, EtOAchexane,1:3) furnishing 3.7916 g of N-Methyl-N-Boc-aminoethanol O-allyl ether ascolorless oil (72% yield). N-Boc deprotection was achieved according to the method ofStrazzolini et al.1 To a 200 mL rbf charged with a magnetic stirbar and CH2Cl2 (22 mL)and immersed in an ice-water bath added 1.48 mL of conc. H2SO4 (assumed to be 17.9 M,26.5 mmol) with stirring. The central neck was plugged with a glass stopcock while adropping funnel was attached to the side-neck. A solution of 3.79 g of N-Methyl-N-BocaminoethanolO-allyl ether (17.6 mmol) in 65 mL CH2Cl2 was added to the solution ofacid dropwise from the addition funnel within 45 min followed by removal of cold bathand stirring at rt for 6 h. The dark purple mixture was transferred into a separatory funneland extracted with water (40 mL). The organic phase was extracted with additional 40mL of water, after which the aqueous extracts were combined in a 200 mL Erlenmeyerflask and basified by addition of NaOH (3.245 g in 15 mL water) with stirring. Theresulting solution was saturated with NaCl and extracted with three 50 mL portions ofCH2Cl2. Combined extracts were dried over Na2SO4, filtered into a 500 mL rbf andstripped of the solvent on the rotary evaporator (200 mm Hg). The resulting yellowish oilwas fractionated in vacuo using a one-piece distillation head and a receiving flask held at-50 C. The title compound was obtained as colorless oil (1.2208 g, 60% yield).

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Reference:
Article; Kultyshev, Roman G.; Miyazawa, Akira; Tetrahedron; vol. 67; 11; (2011); p. 2139 – 2148;,
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