Tag: M.W=100-200

Reference of 83922-54-7, A common heterocyclic compound, 83922-54-7, name is 4-(Methylsulfonamido)benzaldehyde, molecular formula is C8H9NO3S, 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 the compound prepared in Reference Example 2 (100 mg) in dimethyl formamide (3 mL) was added acetic acid (16 muL) (or triethylamine (40 muL)). To the reaction mixture was added N-(4-formylphenyl)methanesulfonamide (56 mg) and sodium triacetoxyborohydride (82 mg). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated, the obtained residue was purified by column chromatography on silica gel (ethyl acetate : methanol = 20 : 1-10 : 1) and 4N hydrogen chloride / ethyl acetate solution was added thereto. The reaction mixture was concentrated to give the compound of the present invention (72 mg) having the following physical data. TLC: Rf 0.67 (dichloromethane:methanol=5:1); NMR(CD3OD): delta 7.53, 7.34, 4.32, 4.15, 3.99, 3.74, 3.54-3.42, 3.33-3.16, 3.01, 2.49-2.24, 2.14- 1.91, 1.80-1.60, 1.40-1.15, 1.00-0.87.

The synthetic route of 83922-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1541574; (2005); A1;,
Amide – Wikipedia,
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Synthetic Route of 14062-80-7,Some common heterocyclic compound, 14062-80-7, name is 4-Chloro-N,N-dimethylbenzamide, molecular formula is C9H10ClNO, 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’-cyanobenzimidamide (16.8 g, 115 mmol),Compound A-2 (21 g, 115 mmol) andPhosphorus oxychloride (12 mL, 128 mmol) was added to a solution ofAnd the mixture was added to 500 mL of acetonitrile, followed by stirring and refluxing for 1 hour. After cooling to room temperature, the resulting solid was filtered, washed with water and ethanol, and dried to give Compound A (27.6 g, yield 80%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-N,N-dimethylbenzamide, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Kang Min-yeong; Park Tae-yun; Cho Seong-mi; Moon Jeong-uk; Jeong Min-u; Lee Jeong-ha; Chae Mi-yeong; (30 pag.)KR2019/9211; (2019); A;,
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Application of 98-64-6, These common heterocyclic compound, 98-64-6, name is 4-Chlorobenzenesulfonamide, 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: The prepared TfOH-SiO2 (60 mg, containing 0.05 mmol TfOH) was added to the toluene (2 mL) solution of alkene (2 mmol or 4 mmol) and sulfonamide (1 mmol) and the reaction mixture was stirred at 70 oC (or 85 oC). The course of the reaction was monitored by TLC. After the completion of the reaction, the mixture was cooled to room temperature and the reactor was centrifuged (2000 r/min) for 2 min and the solution was removed by syringe. The catalyst was then washed with toluene (1 mL) twice with the same procedure and a new reaction was carried out by adding the new batch of alkene (2 mmol), sulfonamide (1 mmol) and toluene (2 mL) to the recovered catalyst. The solution containing the product was purified through a silica gel flash column to afford the product.

The synthetic route of 98-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Pei Nian; Xia, Fei; Zhao, Zheng Le; Wang, Qing Wei; Ren, Yu Jie; Tetrahedron Letters; vol. 52; 46; (2011); p. 6113 – 6117;,
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Related Products of 1888-91-1,Some common heterocyclic compound, 1888-91-1, name is N-Acetylcaprolactam, molecular formula is C8H13NO2, 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 following five acetyl donating compounds were assessed at the outset: [0114] 1. N-acetoxysuccinimide [0115] 2. N-acetylsuccinimide [0116] 3. N-acetylcaprolactam [0117] 4. N,N,N,N-tetraacetylethyidiamine (TAED) [0118] 5. N,N,N-triacetylethylenediamine [0119] 6. Pentaacetylglucose [0120] Among these five compounds, only N-acetylcaprolactam is in the liquid state at ambient temperature. Some of the compounds are available on the market, although it was possible to carry out their synthesis by method available in the state of the art. [0121] From a preliminary assessment, it was observed that: [0122] Although poorly soluble in water, the first two compounds rapidly undergo perhydrolysis, once dispersed in a hydroalcoholic solution based on 3% w/w hydrogen peroxide; however, by being very reactive, they are highly sensitive to air moisture, so much so that their storage requires too severe conditions for use and above all for standard shipping. [0123] The third compound tends to separate at the bottom, once dispersed in a hydrophilic environment; however, it dissolves in the few moments after mixing owing to advancement of the perhydrolysis reaction and the solubilisation of the reaction by-products. This compound is also to be regarded as a medium fast rate N-acetylating agent and does not cause any particular problem, if suitably stored in tight-sealed vessels. [0124] The fourth compound is very well-known in the field of decontaminating, detergent and bleaching formulations and is a fast-rate acetylating agent even though it exhibits little solubility in water, particularly at ambient temperature and when the solution has a neutral-acidic pH. [0125] Finally, the fifth and the sixth compounds from a preliminary assessment were found to be weak acetylating agents and also poorly miscible with water.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Acetylcaprolactam, its application will become more common.

Reference:
Patent; Preto, Andrea; Tabasso, Paolo; US2004/2616; (2004); A1;,
Amide – Wikipedia,
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Electric Literature of 67046-22-4, The chemical industry reduces the impact on the environment during synthesis 67046-22-4, name is 6,7-Dihydro-5H-pyrido[2,3-b]azepin-8(9H)-one, I believe this compound will play a more active role in future production and life.

At -78C, 4.5 mL of 2.0 M lithium diisopropylamide-tetrahydrofuran solution and 300 mg of paraformaldehyde were added to tetrahydrofuran (30 mL) solution of 367 mg of the compound of the above 1, and gradually heated up to room temperature. At room temperature, this was stirred overnight, and then water was added to the reaction liquid and extracted with ethyl acetate. The ethyl acetate layer was dried with anhydrous sodium sulfate, the solvent was evaporated off under reduced pressure, and the residue was separated and purified through partitioning thin-layer chromatography (chloroform/methanol = 10/1) to obtain 111 mg of the entitled compound.

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, 6,7-Dihydro-5H-pyrido[2,3-b]azepin-8(9H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1726590; (2006); A1;,
Amide – Wikipedia,
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Electric Literature of 16982-21-1, 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. 16982-21-1 name is Ethyl 2-amino-2-thioxoacetate, 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.

Ethyl thiooxamate (1.0 Kg, 7.52 mol) was added portion-wise to a solution of 2- bromopyruvic acid (1.38 Kg, 8.27 mol) in THF (4 L) over 20 min while the reaction was cooled with water bath. The reaction mixture was stirred for 12 h at room temperature. The reaction mixture was filtered to remove solid. The filtrate was concentrated to dryness to afford crude compound 70-1 (1.8 kg). The crude 70-1 was triturated with EtOAc/hexane/H20 (1 :3 :2, 6 L), filtered, and the solid was further triturated with EtO Ac/hexane (1 :8, 3 L), filtered, and the solid was dissolved in DCM (6 L), dried over anhydrous Na2S04, concentrated to afford compound 70-1 (617 g, 41% yield based on ethyl thiooxamate) as light yellow solid. 1H NMR (400 MHz, CDCI3): d 8.79 (s, 1H), 4.38-4.46 (q, J= 7.2 Hz, 2H), 1.3-1.38 (t, J= 7.2 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-amino-2-thioxoacetate, and friends who are interested can also refer to it.

Reference:
Patent; ARIAGEN, INC.; COLABUONO, Peter; JOHNSON, Graham; MANNING, David Douglas; WOLF, Mark Allan; (312 pag.)WO2019/99977; (2019); A2;,
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Adding a certain compound to certain chemical reactions, such as: 188345-71-3, name is 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, 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 188345-71-3, Safety of 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene

2.22 Preparation of Compound 4 A stream of O3 was bubbled through a solution of compound 3 (8.0 g, 41 mmol) in CH3CO2H (21 mL) and DCM (350 mL) at -50-60 C. until the solution turned blue. Excess O3 was removed with O2, and Me2S (7.7 mL) was added dropwise to the solution. The mixture was allowed to warm gradually to rt and stirred for 16 h under N2. The solution was concentrated and the residue was used for the next step directly.

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, 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartman, George D.; US2015/132258; (2015); A1;,
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. 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 20348-09-8

EXAMPLE 1096-((l-(2-(3-Oxo-2H-pyrido[3,2-b][l,4]oxazin-4(3H)-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylamino)methyl)-2H-pyrido[3,2-b][l,4]oxazin-3(4H)-oneHydrochlorideStep 1tert-Butyl 1 -(2-(3-Oxo-2H-pyrido[3,2-b] [ 1 ,4]oxazin-4(3H)-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylcarbamateTo a suspension of sodium hydride (38.0 mg, 55%) in N,N-dimethylacetamide (5 mL) was added 2H-pyrido[3,2-b][l,4]oxazin-3(4H)-one (151 mg) under cooling with ice, the mixture was stirred at room temperature for 30 minutes. The mixture was added AC (151 mg) under cooling with ice, the mixture was stirred at room temperature for 1.5 hours and further stirred at 60 C for 4 hours. The mixture was concentrated in vacuo. After dilution of the residue with ethyl acetate, the mixture was added saturated ammonium chloride solution under cooling with ice. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, chloroform : ethyl acetate = 2: 1) of the residue gave tert-butyl l-(2-(3-oxo-2H-pyrido[3,2-b][l,4]oxazin- 4(3H)-yl)ethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate (84.0 mg).1H NMR (CDC13): delta 1.42 (s, 9H), 1.69-2.10 (m, 10H), 3.90 (s, 2H), 4.16-4.29 (m, 3H), 4.62 (d, J= 3.7 Hz, 2H), 6.90 (dd, J= 8.0, 4.9 Hz, 1H), 7.19 (dd, J= 7.3, 1.2 Hz, 1H), 8.01 (dd, J= 4.8, 1.2, Hz, 1H).MS (ESI+) m/z: 404 (MH+).HRMS (ESI+) for C2iH3oN305 (MH+): calcd, 404.21855; found, 404.21800.

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 20348-09-8.

Reference:
Patent; KYORIN PHARMACEUTICAL CO., LTD.; MERCK SHARP & DOHME CORP.; FUKUDA, Yasumichi; KAELIN, David E. Jr.; SINGH, Sheo B.; WO2013/3383; (2013); A1;,
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Application of 3984-14-3, A common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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.

Intermediate 3 1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3H) 1.59-2.04 (m, 7H) 2.74-2.82 (m, 1H) 2.88 (s, 6H) 7.57 (dd, J=8.42, 1.46 Hz, 1H) 7.74 (d, J=8.78 Hz, 1H) 7.91 (s, 1H) 11.71 (s, 1H) 12.08 (s, 1H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 oC for 2 h. After cooling to 30 oC, N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 oC. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 oC. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

The synthetic route of 3984-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/171015; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, 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. Application In Synthesis of 5-Amino-2-methylbenzenesulfonamide

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; WO2006/20564; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics