Month: September 2021

Some common heterocyclic compound, 78191-00-1, name is N-Methoxy-N-methylacetamide, molecular formula is C4H9NO2, 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. Product Details of 78191-00-1

A suspension of 6-bromo-3-isopropyl[1 ,2,4]triazolo[4,3-a]pyridine hydrochloride (1.00 g, 3.62 mmoi) in THF (18.0 mL) was charged with a positive stream of nitrogen and cooled to 0 0C. The resulting suspension was then treated with commercially available solution of isopropylmagnesium chloride in diethyl ether (2.0 M THF solution, 3.5 mL, 7.0 mmol). The internal temperature of the reaction was not allowed to exceed 0 0C. The resulting dark solution was allowed to stir for 1 hour and then the reaction was treated with N-methoxy-N-methyl acetamide. After 4 hours, the reaction was quenched with 100 mL of saturated ammonium chloride solution and was extracted with ethyl acetate (3 X 250 mL). The resulting organic extract was Na2SO4 dried, filtered, and concentrated in vacuo to a residue that was directly subjected to normal phase silica chromatography (60 % ethyl acetate, 30 % hexanes, 10 % MeOH) to furnish a gum (743 mg, 85 %). 1H NMR (300 MHz, O4-MeOH) delta 9.02 (s, 1 H), 7.87 (dd, J= 9.7, 1.5 Hz, 1 H), 7.68 (dd, J= 9.6, 1.1 Hz, 1 H), 3.72 (septet, J = 6.8 Hz, 1 H), 2.68 (s, 3H), 1.51 (d, J= 6.8 Hz1 6H); LC/MS C-18 column, tr = 0.48 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50 0C). ES-MS m/z 204 (M+H). ES-HRMS m/z 204.1158 (M+H calcd for C11H14N3O requires 204.1131).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 78191-00-1, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/18735; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1129-26-6,Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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.

At room temperature, the appropriate amount of organic solvent (volume ratio of 1: DMAC 2 and the mixture of PEG-200), add, Compounds 200mmol formula (II), 15mmol lOOmmol catalyst into the formula (I), (Three mistakes to 12mmol chloride (A1C13) and 3mmol zinc iodide (Znl2) mixture), 80mmol oxidant Phi (TFA) 2,20mmol lOOmmol additives of niobium pentachloride and trifluoromethanesulfonic acid; and then warmed to 80 C, and the reaction was stirred at this temperature for 2 hours;After the [0046] reaction, the reaction system was cooled to room temperature, followed by addition of a saturated aqueous solution of sodium thiosulfate was sufficiently washed with acetone was added and extracted 3 times, the combined organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure , the residue by flash column chromatography on silica gel, ethyl acetate and an equal volume of petroleum ether mixture as eluent, to afford the compound of formula (III), in a yield of 96.9%

The synthetic route of 1129-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang Wei; Zhang, Wei; (10 pag.)CN105294518; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 72179-84-1, name is (Methylsulfamoyl)amine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: CH6N2O2S

A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. N-methylsulfamide (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.

The synthetic route of 72179-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/130057; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 123986-64-1, 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 123986-64-1 as follows.

General procedure: The solution of (R)-1-(6-(4-(1-(3-hydroxybenzyl)-3-methyl-1H-thieno[2,3-c]pyrazole-5-carbonyl)-2-methylpiperazinmethylpiperazin-1-yl)pyridin-3-yl)ethanone (9b) (0.059 g, 120 mumol) in THF (1.0 mL)was added to tert-butyl(2-hydroxyethyl)carbamate (29.0 mg, 180 mumol), polymer supported PPh3(3 mmol/g, 120 mg) and di-2-methoxyethyl azodicarboxylate (0.051 g, 216 mumol).The mixture was stirred at room temperature for 2 h. Then, polymer supportedPPh3 (3 mmol/g, 60 mg) and the solution of di-2-methoxyethylazodicarboxylate (0.051 g, 216 mumol) in THF (0.10 mL) were added to thereaction mixture. The mixture was stirred at room temperature for 1 h. Thesolvent was evaporated by blowing away with the air at 50 C. The residue waspoured into toluene (3.0 mL) and water (1.0 mL), and stirred for 5 min. Theorganic layer was filtered on Top-Phase Separation Filter Tube, and thefiltrate was evaporated by blowing away with the air at 60 C. The residue waspurified by preparative HPLC (Actus Triart C18, eluted with MeCN/10 mM NH4HCO3aq. 10:90?100:0). Pure fractions were combined and concentrated byblowing away with the air at 50 C. The intermediate was dissolved into EtOAc(0.50 mL) and 4M HCl-EtOAc (1.0 mL) was added to the solution at room temperature.The mixture was shaken at room temperature for 10 min. Then the mixture wasevaporated by blowing away with the air at 50 C. The solution of BODIPY FLpropionic acid 1 (0.020 g, 69 mumol)in DMA (0.50 mL) and the solution of WSC(HCl) (0.016 g, 84 mumol) and HOBt(0.011 g, 84 mumol) in DMA (0.500 mL) and iPr2NEt(84 mL, 480 umol) were added to the mixture. The mixturewas stirred at room temperature for 2 h. The reaction mixture was diluted withEtOAc (3.0 mL) and quenched with water (1.0 mL), and stirred for 2 min. Theorganic layer was separated and then the aqueous layer was extracted with EtOAc(2.0 mL). The combined organic layer was evaporated by blowing away with theair at 50 C. The residue was purified by preparative HPLC (Actus Triart C18,eluted with MeCN/10 mM NH4HCO3 aq. 5:95?100:0). Purefractions were combined and concentrated by blowing away with the air at 50 Cto give the product 10 (8 mg, 9.9 mmol, 1 %).

According to the analysis of related databases, 123986-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Katoh, Taisuke; Yoshikawa, Masato; Yamamoto, Takeshi; Arai, Ryosuke; Nii, Noriyuki; Tomata, Yoshihide; Suzuki, Shinkichi; Koyama, Ryoukichi; Negoro, Nobuyuki; Yogo, Takatoshi; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1145 – 1148;,
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. 437998-34-0, name is 2-Amino-3-bromobenzamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7BrN2O

General procedure: 2-Aminobenzamides (1 mmol) and 1,1-dichloro-2-nitroethene (1.2 mmol) were added to 5 mL of water in a 25 mL round-bottom flask. Then stirred at corresponding temperature and corresponding reaction time, after completion, the product precipitated from the reaction mixture and can be easily separated by filtration, then give the pure products.

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; Zhu, Fengjuan; Song, Runjiang; Li, Shen; Shao, Xusheng; Synlett; vol. 27; 14; (2016); p. 2167 – 2170;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 17641-08-6, 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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To the appropriate Schiff bases of isatin (10 mmol) in8-10 cm3 of anhydrous DMF, K2CO3 (15 mmol) was addedand stirred at room temperature for 1 h. After completion of1 h, the solution turned red brown in color. Appropriatechloroanilides (10 mmol) and KI (2 mmol) were then addedto this solution drop wise and heated at 60 C for 5.5-9 h.After conforming the end of reaction by TLC (ethyl acetate:n-hexane 30:70), the mixture was poured into ice cold water.Precipitated crude product was filtered and washed thoroughlywith cold water (3 9 200 cm3). Compounds wererecrystallized from ethanol/water mixture (1:1). Reactiontimes, melting points, and yields are depicted in Table 1.

The synthetic route of 2-Chloro-N-(3-methoxyphenyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Debnath, Biplab; Ganguly, Swastika; Monatshefte fur Chemie; vol. 147; 3; (2016); p. 565 – 574;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 35303-76-5, The chemical industry reduces the impact on the environment during synthesis 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A solution of 4-(2-aminoethyl)benzenesulfonamide (80 mg, 0.40 mmol), AcOH (0.05 mL) and di-tert-butyl 4-(2-bromoacetamido)-4-(3-(tert-butoxy)-3- oxopropyl)heptanedioate (447 mg, 0.81 mmol) in DCE (20 mL) was stirred at 80 °C for 30 min under nitrogen. The reaction mixture was cooled to 0 °C, and treated with NaBH(QAc)3 (0,254 g, 1 ,2 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by biotage over silica gel to afford the desired product (322 mg, 63percent). NMR (400 MHz, DMSO-d6) 7.77 (s, 2 H), 7.64 (d, J – 8.0 Hz, 2 H), 7.23 (s. 2 H), 7.21 (d, J = 8.4 Hz, 2 H), 7.01 (s, 2 H), 6.80 (s. 2 H), 4.57 (s. 4 H), 3.61 (s, 4 H), 2.79-2,62 (m, 4 H), 2,09 (t, J = 8.0 Hz, 12 H), 1.76 (t, J = 8.0 Hz, 12 H), 1.32 (s, 54 H); MS (ESI), 636.5 (M/2+H)+.

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-(2-Aminoethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MOLECULAR INSIGHT PHARMACEUTICALS; BABICH, John, W; ZIMMERMAN, Craig; JOYAL, John; LU, Genliang; HILLIER, Shawn; MARESCA, Kevin, P; MARQUIS, John; WO2013/103813; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

A round-bottom flask was charged with triphosgene (1.68 g, 5.66 mmol) and DCM (200 mL). Hexafluoroisopropanol (1.93 mL, 18.4 mmol) was added dropwise over 1 min. DIPEA(4.9 mL, 28.0 mmol) was added dropwise over 3 min. The flask contents were stirred at rt for 2 h. tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (3.00 g, 14.2 mmol) was added in one portion, and the reaction mixture was allowed to stir for 18 h at rt. The reaction mixture was then washed with 1 N HCl and brine. The organics were dried over anhydrous NazS04 and concentrated. The resulting oil was chromatographed on a silica column with a gradient (100% hexanes to 80% hexanes/20% acetone) to provide 2-tert-butyl5-(1,1,1,3,3,3-hexafluoropropan-2-yl) tetrahydropyrrolo[3,4-c]pyrrole-2,5(1H,3H)-dicarboxylate (5.74 g, 82%). 1H NMR (400 MHz,Chloroform-d) 0 5.87-5.66 (m, 1H), 3.85-3.70 (m, 2H), 3.70-3.55 (m, 2H), 3.46-3.37 (m,2H), 3.37- 3.17 (m, 2H), 2.96 (br s, 2H), 1.52 (s, 9H). ). LCMS (ESI, m/z): 429.0 [M+Ht.

The synthetic route of 141449-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; JONES, Todd, K.; CISAR, Justin, S.; GRICE, Cheryl, A.; WANG, Dong-Hui; WEBER, Olivia, D.; WO2015/3002; (2015); 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. 98-64-6, name is 4-Chlorobenzenesulfonamide, A new synthetic method of this compound is introduced below., Quality Control of 4-Chlorobenzenesulfonamide

General procedure: The synthesis route of compounds 1-24 followed the general pathway outlined in Scheme 1. The substituted nicotinic acid (1 mmol) mixed with benzenesulfonamide (1 mmol) through by using 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC*HCl) (1.2 mmol) and 4-dimethylaminopyridine (DMAP) (1.2 mmol) in anhydrous CH2Cl2 for 6-8 h at 70-80 °C. The reaction was monitored by TLC. The products are extracted with ethyl acetate. The extract is washed successively with 1 N HCl, water, 1 M NaHCO3, and water, dried over MgSO4, filtered and evaporated. The residue is purified by column chromatography using petroleum ether and ethyl acetate (1:1).

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; Zhang, Hui; Lu, Xiang; Zhang, Li-Rong; Liu, Jia-Jia; Yang, Xian-Hui; Wang, Xiao-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 4; (2012); p. 1411 – 1416;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 109903-35-7, 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. 109903-35-7 name is 4-Amino-N-methylbenzenemethanesulfonamide, 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.

Example 23: 1-(4-{[5-acetyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)- ylidene]amino}phenyl)-lambda/-methylmethanesulfonamide hydrochloride; A mixture of 4-amino-N-methyl-alpha-toluenesulphonamide (200mg, I .Ommol), ethyl isothiocycanate (104mg, 1.20mmol, 0.1 ml) and triethylamine (0.2ml) in ethanol (5ml) was stirred at reflux for 2 hours. The solvent was then removed by rotary evaporation, the resulting material was then suspended in toluene (5ml) and treated with 3-chloro-2,4- pentanedione (0.14g, 1.05mmol, 0.13ml) and the whole mix stirred at 9O0C (oil bath temperature) for 3 hours, and allowed to cool. The reaction mix was filtered and the filtrate evaporated under reduced pressure to give a yellow oil, which was purified by MDAP (mass directed auto-preparation). The relevant fractions were combined and the solvent removed by rotary evaporation to give a brown oil, which was dissolved in dichloromethane (1 ml) and treated with 1 M ethereal HCI (1 ml). The solvent was removed by air drying. The product was triturated in ether, the liquid was decanted off and the residual material was vacuum oven dried to give the title compound as a beige coloured solid (98mg, 24%).LC/MS (ES): Found 368 (ES+), retention time 2.35mins. Ci6H2IN3O3S2 requires 367. 1 H-NMR (400MHz, MeOD-d4): delta 1.49 (3H, t, J=7Hz), 2.52 (3H, s), 2.71 (3H, s), 2.76 (3H, s), 4.31 (2H, m), 4.42 (2H, s), 7.55 (2H, m), 7.66 (2H, d, J=8Hz).

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53448; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics