Tag: M.W=100-200

Electric Literature of 98-18-0, A common heterocyclic compound, 98-18-0, name is 3-Aminobenzenesulfonamide, molecular formula is C6H8N2O2S, 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.

First the starting material, 3-isothiocyanato-benzenesulfonamide, which has the structural formula was prepared as follows. To a solution of 3-AMINO- benzenesulfonamide (Maybridge Chemical Co. , 1.00 g, 5.81 MMOL) in acetone (15 mL) at 0°C was added sequentially thiophosgene (0.503 mL, 6.39 MMOL) and fresh 25percent aq. NA2CO3 (5. 8 mL). The mixture was allowed to warm to ambient temperature. After 20 minutes, the acetone was removed under reduced pressure. The resultant suspension was adjusted to pH=7 with 10percent aq. HCI and filtered to isolate a light tan solid, 1.24 G (quantitative yield), that matched previous (mp 146-149°C ; French patent application FR 1528249; Chem. Abs. , 71, 30206 (1969) ) and was used without further purification. 1H NMR (DMSO-d6) : 87. 83-7.75 (1H, m), 7.69-7. 62 (1H, m), 7.52 (1H, s). The title compound was prepared in a manner similar to that for 4- [4-AMINO-5- (2- hydroxy-2-methyl-propionyl)-thiazol-2-ylamino]-benzenesulfonamide (Example M (1)). 3- ISOTHIOCYANATO-BENZENESULFONAMIDE (212 mg, 0.989 MMOL) furnished a yellow solid, 432 mg, that precipitated from IPROH/HEX to give 17. 1 mg of orange-brown solid. Furthermore, the mother liquor was purified via column, chromatography with a 5-10percent MeOH/CHCI3 stepwise gradient eluant to provide 120 mg of yellow solid that decomposed above 240 C. The total yield was 291 mg (73percent). 1H NMR (CD30D) : 8 8.36 (1H, dd, J = 1.8, 1.8 Hz), 7.78 (1H, ddd, J = 1.0, 2.2, 8.1 Hz), 7.62 (1H, ddd, J = 1. 1,1. 6,7. 8 HZ), 7.50 (1H, t, J = 8. 1 Hz), 7.05 (2H, t, J = 7. 5 HZ). FTIR (KBr): 3309,3076, 1620, 1546,1527, 1465,1429, 1156 cm-1. HRFABMS: Calcd for CR6H 3F2N403S2 (M+H+) 411.0406. Found: 411.0406. Anal. calcd. for CA6HR2F2N403S2 0. 5 H2O : C, 45.82 ; H, 3.12 ; N, 13.36 ; S, 15.29. Found: C, 45.78 ; H, 3.12 ; N, 13.18 ; S, 15.50.

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/72070; (2004); A1;,
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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 683-57-8 as follows. Product Details of 683-57-8

Example 1: 2-[1-(2-Morpholin-4-yl-ethoxy)-naphthalen-2-ylamino]-acetamide, hydrochloride; [Show Image] 2-Bromoacetamide (1.05 equiv), potassium carbonate (1.5 equiv) and sodium iodide (0.1 equiv) were added at r.t. to a solution of 1-(2-Morpholin-4-yl-ethoxy)-naphthalen-2-ylamine (50 mg, 0.18 mmol) in acetonitrile (3 mL). The resulting mixture was allowed to heat to 80C for 18 hours. water (10 mL) and DCM (10 mL) were added to the mixture. The organic layer was washed with water (1x) and brine (2x). After drying over MgSO4, the solvent was evaporated to afford the crude compound. This latter was purified by flash chromatography (100% EtOAc to 10% MeOH/EtOAC) to afford brown oil in 63 % yield. A 2.0 M solution of HCl in ether (10 equiv) was added to a solution of this latter in 0.5 mL of methanol to afford the HCl salt as an brown hygroscopic solid. 1H NMR (400 MHz, CD3OD) : 3.38 (s, 2H, CH2-N), 3.86 (t, J 4.9 Hz, 4H, CH2-N), 4.0-4.1 (m, 4H, CH2-O), 4.14 (s, 2H, NH-CH2-CO), 4.57 (t, J 4.8 Hz, 2H, CH2-CO), 7.31 (d, J 9.3 Hz, 1H, Ar), 7.45 (m, 1H, Ar), 7.60 (m, 1H, Ar), 7.60 (m, 1H, Ar), 7.77 (d, J 8.8 Hz, 1H, Ar), 7.90 (d, J 7.8 Hz, 1H, Ar), 8.02 (d, J 9.3 Hz, 1H, Ar). M/Z (M+H)+ = 330.

According to the analysis of related databases, 683-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Faust Pharmaceuticals; EP1777219; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 63920-73-0, 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. 63920-73-0 name is 2-Amino-4,6-dimethoxybenzamide, 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.

To a solution of 2-hydroxymethyl-benzofuran-5-carbaldehyde (0.450 g, 2.55 mmol) and 2-amino-4,6-dimethoxybenzamide (0.500 g, 2.55 mmol) in N,N-dimethylacetamide (5 mL) were added sodium hydrogen sulfite (58.5%; 0.510 g, 2.80 mmol) and p-toluenesulfonic acid (50 mg, 0.25 mmol). The reaction mixture was stirred at 120 C. for 6 hours under nitrogen and cooled to room temperature. The separated solid was filtered, washed with ether (30 mL), water (30 mL), and ethyl acetate (20 mL), and then dried under vacuum to give the title compound as a yellow solid. Yield: 0.572 g (64%). 1H NMR (400 MHz, DMSO-d6): delta 12.07 (br s, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.10 (dd, J=8.8 and 1.6 Hz, 1H), 7.67 (d, J=8.8 Hz, 1H), 6.89 (s, 1H), 6.76 (d, J=2.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 4.61 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H). MS (ES+) m/z: 353.20 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,6-dimethoxybenzamide, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281398; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 62009-47-6, The chemical industry reduces the impact on the environment during synthesis 62009-47-6, name is 2-Aminomalonamide, I believe this compound will play a more active role in future production and life.

EXAMPLE 10 In 2.1 mL of water is suspended 0.5 g of 2-aminomalonamide. Under ice-cooling, 0.43 g of ethyl glyoxalate is added to the suspension, which is then stirred for 40 minutes. Then, 0.85 mL of 5 mol/mL sodium hydroxide is added to the resulting suspension, which is then stirred at the same temperature as above for 40 minutes. The reaction mixture is adjusted to pH 12 by adding 1 mol/L sodium hydroxide, and once made into a solution. The solution is then adjusted to pH 2 by adding 6 mol/mL hydrochloric acid. The deposited crystals are collected by filtration and washed successively with water and 50% (w/w) ethanol to obtain 0.15 g of 3,5-dihydroxy-2-pyrazinecarboxamide. IR(KBr) cm-1: 1660 NMR(D2O) delta value: 6.97(1H,s)

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

Reference:
Patent; Furuta, Yousuke; Egawa, Hiroyuki; Nomura, Nobuhiko; US2002/13316; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1524-40-9, name is 3-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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. SDS of cas: 1524-40-9

(1) 0.0040g iridium catalyst [Cp * IrCl2] 2,0.0076 g silver salt bis(trifluoromethanesulfonyl)imide silver,0.825g oxidant silver acetate,31.4muLacetophenone-O-methyl oxime and0.07 g of m-fluorobenzenesulfonamide was placed in a reaction tube.Add 2mL of dichloromethane as a solvent,Heating and stirring reaction,The temperature of heating and stirring is 60C.Reaction time 24h.(2) After the reaction is over,Separation by column chromatography (300-400 column chromatography silica gel column packing,Eluent: ethyl acetate: petroleum ether = 12:100 v/v),Can get the product N-[2-(1-Methoxyimino)ethyl]phenyl-3-fluorobenzenesulfonamide.The yield is 83%.The structural characterization of the products are shown in Figures 21 and 22, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1524-40-9, its application will become more common.

Reference:
Patent; University of Jinan; Zhao Huaiqing; Zhang Wei; Xu Xiangwen; Wu Wei; (40 pag.)CN107739322; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 617-36-7, The chemical industry reduces the impact on the environment during synthesis 617-36-7, name is Ethyl 2-amino-2-oxoacetate, I believe this compound will play a more active role in future production and life.

Step 1: Preparation of N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamide Into a 3-neck, 250 ml, round bottom flask was added 30.5 g (0.25 mole) of ethyl oxamate (Aldrich Chemical Company) and 100 ml of methanol. The flask was equipped with a magnetic stirrer, thermometer, reflux condenser and addition funnel containing 39.0g (0.25 mole) 4-amino-2,2,6,6-tetramethylpiperidine. The stirrer was activated and the amine was added dropwise to the ethyl oxamate solution over 12 minutes as the temperature slowly rose to 35C. The reaction was stirred an additional 2.5 hours and filtered. After air drying overnight, the filter cake weighed 40.4g and had a melting point of 203-208C. The filtrate was transferred back to the 250 ml 3-neck flask and another 30.5g of ethyl oxamate was added. An additional 39g of 4-amino-2,2,6,6-tetramethylpiperidine were added over 7 minutes as the temperature slowly rose to 28C. The reaction was stirred 3 hours and filtered. After air drying overnight, the filter cake weighed 50.0g and had a melting point of 198-200C. The infrared spectrum (nujol mull) of the product contained a sharp NH band at 3370 cmmin1, a strong broad carbonyl band at 1670 cmmin1 and a weaker carbonyl band at 1520 cmmin1.

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, Ethyl 2-amino-2-oxoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELF ATOCHEM NORTH AMERICA, INC.; EP516192; (1992); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 2895-21-8, 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. 2895-21-8 name is N-Isopropyl-2-chloroacetamide, 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.

To a solution of /c/7-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2- methoxyethoxy) quinazolin-4-ylamino)-1H-indazole-l -carboxylate (0.40Og, 0.72 mmol) and 2-chloro-N-isopropylacetamide (0.107g, 0.79 mmol) in DMF ( 16 mL) was added K.2CO3 (0.297g, 1.44 mmol). The mixture was heated at 80 C for 72 h. The mixture was concentrated in vacuo and taken on directly into the next step. HPLC retention time 6.76mins^

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

Reference:
Patent; SURFACE LOGIX, INC.; SWEETNAM, Paul; BARTOLOZZI, Alessandra; CAMPBELL, Anthony; COLE, Bridget; FOUDOULAKIS, Hope; KIRK, Brian; SESHADRI, Hemalatha; RAM, Siya; WO2010/104851; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 40545-33-3, These common heterocyclic compound, 40545-33-3, name is 2-Amino-5-methylbenzamide, 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 15 mL tube was added 2-aminobenzamide (1 mmol), benzyl amine (1.5 mmol), and a stir bar. Then H2O2 (30 wt% in H2O, 5 equiv.) was added by a syringe at room temperature under open air. The tube was closed and kept at 120C for 20 h. The conversion and yield were determined by GC and GC-MS using hexadecane (0.1 mmol) as the internal standard.

Statistics shows that 2-Amino-5-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 40545-33-3.

Reference:
Article; Qi, Xin-Xin; Song, Zhen-Zhen; Gong, Jin-Long; Fang, Zheng-Yu; Wu, Xiao-Feng; Chinese Chemical Letters; vol. 27; 1; (2016); p. 21 – 24;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 119023-25-5, name is 2-Amino-4-fluorobenzamide, 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 119023-25-5, name: 2-Amino-4-fluorobenzamide

Stage 3: 2-aminomethyl-5-fluorophenylamine 2 M borane-dimethyl sulfide complex (40 ml, 80 mmol) in tetrahydrofuran was added to a solution of the product from stage 2 (2.45 g, 16 mmol) in anhydrous tetrahydrofuran (50 ml) and the mixture was heated under reflux for 9 hours. Water (4 ml) was cautiously added to the cooled reaction solution and the mixture was then concentrated in vacuo. Toluene (2*) was added to the residue and the mixture was concentrated again each time. The residue was then repeatedly dissolved in methanol (3*) and concentrated each time. The crude product was purified by flash chromatography with chloroform/methanol (7:3) and 1% triethylamine. Yield: 1.37 g (61%), white solid. Melting point: 49-51 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-fluorobenzamide, and friends who are interested can also refer to it.

Reference:
Patent; Gruenenthal GmbH; US2008/293749; (2008); 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. 630-22-8, name is 2,2-Dimethylpropanethioamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 630-22-8

Example 23; N-[2-Chloro-3-(2-(1,1-dimethylethyl)-5-{2-[(2-methylpropyl)amino]-4-pyrimidinyl}-1,3-thiazol-4-yl)phenyl]-2,5-difluorobenzenesulfonamide; Step A: N-{2-Chloro-3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,5-difluorobenzenesulfonamide; To a solution of N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide (3.0 g, 6.55 mmol) in DMA (25 mL) was added NBS (1.165 g, 6.55 mmol). After stirring for 1 h at rt, 2,2-dimethylpropanethioamide (0.767 g, 6.55 mmol) was added and the reaction mixture was stirred at 80 C. for 2 h. The reaction mixture was diluted with EtOAc (100 mL) and extracted five times with water. The organic layer was dried over anhydrous NaSO4, adsorbed onto silica gel, and purified via column chromatography, eluting with 0-50% EtOAc/DCM. The desired fractions were combined and concentrated to generate 1.31 g (2.36 mmol, 36.0% yield) of the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6): delta 10.74 (s, 1H), 8.56 (d, J=5.4 Hz, 1H), 7.41-7.58 (m, 6H), 6.57 (d, J=5.4 Hz, 1H), 1.42 (s, 9H). MS (ESI): 555.0 [M+H]+.

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 630-22-8.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics