Month: March 2021

3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H6N2O2

After 80 parts of water was added to 4- (manufactured by Tokyo Kasei Kogyo Co., Ltd.) amino phthalimide 16.2 parts, 0.4 parts of sodium hydroxide was added and dissolved.Under ice cooling, 35% aqueous sodium nitrite solution 19.7 parts was added, followed by 35% hydrochloric acid 26.2 parts was stirred for 2 hours and dissolved by adding little by little to obtain a suspension containing a diazonium salt.[0068]Then, 23.9 parts of 6-amino-4-hydroxy-2-naphthalenesulfonic acid was suspended in 100 parts of water, with sodium hydroxide, the pH was adjusted to 9.0.Here it was added dropwise by a pump over a period of suspension 15 minutes including the diazonium salt.After completion of the addition, to obtain a suspension of yellow by stirring for an additional 30 minutes.After stirring for 1 hour the suspension was stirred for 1 hour.The obtained filtered red solid was dried under reduced pressure at 60 C., to obtain a compound represented by formula (I-1) 40.5 parts.Measurement of the maximum absorption wavelength of this compound, lambdamax was 545nm.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company Limited; Ashida, Toru; (22 pag.)JP5831135; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives 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 3676-85-5, Computed Properties of C8H6N2O2

2.0 parts of a formyl derivative represented by the following formula (2) and 2.0 parts of 4-aminophthalimide represented by the following formula (3) are added to 20 parts of acetic acid and stirred at 40 C. for 6 hours The solution thus obtained was cooled to room temperature, poured into 50 parts of water, stirred for 30 minutes, and the precipitated solid was collected by filtration, washed with water and dried to obtain No. 1 of the above specific example. 1.5 parts of a methine compound (lambda max: 435 nm) represented by 1 was obtained.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NIPPON KAYAKU COMPANY LIMITED; TAKAHASHI, MASAYUKI; (14 pag.)JP2015/189767; (2015); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Potassium 1,3-dioxoisoindolin-2-ide

Compound 4 (1.86g, 10mmol) and 1,6-b hexyl bromide (12.2g, 50mmol) in dry DMF (10 ml) and heated to 100 C, thermal insulation 12h. Then the excess is removed by reduced pressure distillation 1,6-b hexyl bromide. The silica gel column for separation and purification of the crude product (showering liquid is ethyl acetate/petroleum ether, volume ratio of 1:40), be 2.5g compound 5 (colorless powder), yield 81%.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hecheng Advanced Materials Co., Ltd; Kongxiang, Fei; Huang, Da; Wanggui, Xia; Liu, Canhui; Tan, Yudong; (22 pag.)CN105461628; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 446292-08-6,Some common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, molecular formula is C22H19N3O6, 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.

Methyl amine (40 % strength, 153.2 ml) is added to suspension of 2- ({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (150 gm) in methanol (1500 ml) at 25 to 30 C. The reaction mass was then refluxed for 6 hr. After completion of reaction, the reaction mass was cooled to 25-30 C, the pH of reaction mass was adjusted to 2-3 using cone. HCl. Reaction mass was stirred for 1 hr & filtered off the solid. The solid obtained was washed with methanol (50 ml) Obtained solid was dissolved in mixture of methanol (500 ml) and methylene dichloride (750 ml) by adjusting pH of reaction mass to 7-8 using triethylamine at 25-30 C and stirred till clear solution was obtained, pH of reaction mass was adjusted to 4-5 by using acetic acid at 25-30 C. Reaction mass was stirred for 1 h at 25-30 C and filtered off the solid. The solid obtained was washed with methanol (50 ml) and dried under vacuum at 50 to 55 C for 5 hr to obtain 4-{4-[(5S)-5-(aminomethyl)-2-oxo- 1 ,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride. [Yield = 92.4 gm (80 %); Purity (HPLC) = 98.0 %]

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEGAFINE PHARMA (P) LTD; MATHAD Vijayavitthal Thippannachar; PATIL NILESH SUDHIR, Nilesh; NIPHADE NAVNATH CHINTAMAN, Navnath; MALI ANIL CHATURLAL, Anil; BODAKE MAHENDRA BHAGIRATH, Mahendra; IPPAR SHARAD SUBHASH, Sharad; TALLA RAJESH, Rajesh; WO2013/121436; (2013); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15861-30-0, 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 15861-30-0 as follows.

To a solution of indoline-5-carboxylic acid (1 1 .61 mg, 71 .18 gmol) in DCM (0.5 ml_) were added DIPEA (27.60 mg, 213.55 gmol) and HATU (40.60 mg, 106.77 gmol) at 25 C. The mixture was stirred at 25 C for 1 hr and then (2S)-2-amino-4-methylsulfanyl-N-(4-phenylthiazol-2-yl) butanamide (30.0 mg, 71 .1 8 gmol) was added. The reaction mixture was stirred at 25 C for 16 hr. The reaction mixture was concentrated in vacuum to give a residue. The residue was purified through reverse phase-HPLC (FA condition) and followed by prep-TLC (PE/EA=1 /1 ) to afford compound 80 as a white solid. 1 HNMR (400 MHz, MeOD) d = 7.88-7.86 (m, 2H), 7.63-7.59 (m, 2H), 7.39-7.36 (m, 3H), 7.28-7.26 (m, 1 H), 6.58-6.52 (m, 1 H), 4.89-4.86 (m, 1 H), 3.59-3.54 (m, 2H), 3.04-3.00 (m, 2H), 2.68-2.63 (m, 2H), 2.20 – 2.12 (m, 2H), 2.1 1 (s, 3H) ppm. LCMS (ESI) m/z: [M+H]+ = 453.0. Chiral HPLC: Cellucoat-MeOH+ACN(DEA)-40-5min-3mL-35T, 1 .444 min.

According to the analysis of related databases, 15861-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 239463-85-5, The chemical industry reduces the impact on the environment during synthesis 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, I believe this compound will play a more active role in future production and life.

A solution of 500 g of 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1Hindole-7-nitrile tartrate (Compound SM1) was added to 3.0 L of dichloromethane with stirring, then,an aqueous solution (4.0 L) of potassium carbonate (1.105 kg) 221 g of (Boc) 2O, after completion ofthe dropwise addition, 15 to 25 C for 5 hours, standing still liquid, dichloromethane phase with 0.2mol / L HCl solution 3L, saturated sodium bicarbonate solution 2L, saturated brine 2L, then dried overanhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure to give457 g of compound V with an HPLC purity of 99.57%;

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, (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Qilu Pharmaceutical Co., Ltd; Leng, Chuanxen; Fan, Chuanwen; Fang, Xi; Lin, Dong; Liu, Peiyuan; (14 pag.)CN106045892; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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. Quality Control of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of Yb(OTf)3 (0.01 mmol) and ligand L6 (0.02 mmol) wasstirred at r.t. for 2 h in CH2Cl2 (2 mL). The appropriate enones 1 (1mmol) and isatins 2 (0.1 mmol) were then added. The resulting mixturewas stirred at r.t. After the reaction was completed as monitoredby TLC (eluent: hexane-EtOAc, 1:1), the reaction mixture was purifiedby column chromatography (silica gel, eluent: mixture ofhexane and EtOAc).

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Lu; Daka, Philias; Sarkisian, Ryan; Deng, Yongming; Wheeler, Kraig; Wang, Hong; Synthesis; vol. 46; 10; (2014); p. 1339 – 1347;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7699-18-5, 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. 7699-18-5 name is 5-Methoxyindolin-2-one, 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.

An oven-dried flask was charged with BBr3.SMe2 (2.80 g, 9.20 mmol) and 1,2-dichloroethane (15 mL). 5-Methoxyindolin-2-one (0.3Og, 1.84 mmol) was then added and the mixture was heated to reflux for 18 hours. The reaction was then cooled to room temperature and quenched with MeOH (1.0 mL). The mixture was then extracted into EtOAc washing with brine (3X). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo; the resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/Me0H) to give 144 mg, 53 % of a beige powder. MS ESI 149.9 [M + H]+, calcd for [C8H7NO2+ H]+ 150.06

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methoxyindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4, 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. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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.

General procedure: To a solution of isatin (0.2 mmol) and indole (0.2 mmol) in pyridine (0.5 mL) was added K2CO3 (0.2 mmol) under an airatmosphere and the mixture was stirred at 40C for 2 h. Then,morpholine (0.3 mmol), CuI (0.04 mmol), and benzoic acid(0.1 mmol) were added to the reaction mixture and the resultingmixture was heated at 80C for another 5 h. The reaction mixturewas concentrated under reduced pressure. The residue was puriedby ash chromatography on silica gel (eluent: EtOAc/PE 1:1) toyield the corresponding product 4a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Peng, Xiangjun; Xu, Xianyun; Chen, Shuangyang; Tian, Zeng; Liu, Liangxian; Liu, Qian; Tetrahedron; vol. 74; 13; (2018); p. 1505 – 1512;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem