Category: 222036-66-0

Application of 222036-66-0,Chemistry involves the study of all things chemical – chemical processes, chemical compositions and chemical manipulation – in order to better understand the way in which materials are structured, how they change and how they react in certain situations.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

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Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-one, 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. name: 5-Aminoisoindolin-1-one

Synthesis of 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) A mixture of 6-chloro-9H-purine (1, 0.15 g, 0.97 mmol), 5-aminoisoindoline-1-one (2, 0.14 g, 0.97 mmol) and (1S)-(+)-camphor-10-sulfonic acid (0.27 g, 1.16 mmol) in isopropanol (10 mL) was heated in a sealed tube at 100° C. for 4 h. After completion of the reaction, the mixture was concentrated. The obtained solid was filtered and re-crystallized from ethanol and isopropanol to afford 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) as off-white solid. Yield: 0.15 g, 58percent; MS (ESI) m/z 267 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 8.66 (s, 2H), 8.44 (s, 1H), 8.31 (d, J=1.9 Hz, 1H), 7.99 (dd, J=8.3, 1.8 Hz, 1H), 7.67 (d, J=8.3 Hz, 1H), 4.40 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 222036-66-0, its application will become more common.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-one, 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 222036-66-0, category: indolines-derivatives

p-TSA monohydrate (23.12 mg, 0.122 mmol) was added to a stirred solution of 1-(4-((2-chloropyrimidin-4-yl)oxy)naphthalen-1 -yl)-3-(1 -(p-tolyl)-3-(tri methylsi lyl)-1 H-pyrazol-5-yl)urea (see Example 6(i) above; 33 mg, 0.061 mmcl) and 5-aminoisoindolin-1-one (18.01 mg, 0.122 mmol) in THFDMF (1 mL, 1:1). The resulting mixture was heated at 60 °C overnight. The reaction was cooled to rt then diluted with EtOAc (15 mL). The suspension was filtered, the product was detected in the filtrate which was subsequentlyconcentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g column, 0-10percent MeOH in DCM) to afford a white solid. The crude product was purified by preparative HPLC (Waters, Acidic (0.1percent Formic acid), Waters X-Select PrepC18, 5 pm, 19×50 mm column, 35-75percent MeCN in Water) to afford the title compound (7 mg) as a white solid.1H NMR (DMSO-d6) 400 MHz, O: 9.93 (s, 1H), 9.24 (s, 1H), 8.84 (s, 1H), 8.47 (d, 1H),8.22 (s, 1H), 8.11 (d, 1H), 8.00 (d, 1H), 7.82-7.80 (m, 1H), 7.65-7.61 (m, 1H), 7.58-7.54(m, 1H), 7.53-7.36 (m, 6H), 7.34-7.25 (m, 2H), 6.70 (d, 1H), 6.65 (s, 1H), 3.99 (s, 2H),2.41 (s, 3H), 0.27 (s, 9H).LCMS mz 655 (M+H)+ (ES+).

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; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew, Colin, Thor; MEGHANI, Premji; THOM, Stephen, Malcolm; WO2014/33449; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-one, molecular formula is C8H8N2O, 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. Safety of 5-Aminoisoindolin-1-one

Synthesis of 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) A mixture of 6-chloro-9H-purine (1, 0.15 g, 0.97 mmol), 5-aminoisoindoline-1-one (2, 0.14 g, 0.97 mmol) and (1S)-(+)-camphor-10-sulfonic acid (0.27 g, 1.16 mmol) in isopropanol (10 mL) was heated in a sealed tube at 100° C. for 4 h. After completion of the reaction, the mixture was concentrated. The obtained solid was filtered and re-crystallized from ethanol and isopropanol to afford 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) as off-white solid. Yield: 0.15 g, 58percent; MS (ESI) m/z 267 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 8.66 (s, 2H), 8.44 (s, 1H), 8.31 (d, J=1.9 Hz, 1H), 7.99 (dd, J=8.3, 1.8 Hz, 1H), 7.67 (d, J=8.3 Hz, 1H), 4.40 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 222036-66-0, its application will become more common.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-one, molecular formula is C8H8N2O, 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. Safety of 5-Aminoisoindolin-1-one

Synthesis of 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) A mixture of 6-chloro-9H-purine (1, 0.15 g, 0.97 mmol), 5-aminoisoindoline-1-one (2, 0.14 g, 0.97 mmol) and (1S)-(+)-camphor-10-sulfonic acid (0.27 g, 1.16 mmol) in isopropanol (10 mL) was heated in a sealed tube at 100° C. for 4 h. After completion of the reaction, the mixture was concentrated. The obtained solid was filtered and re-crystallized from ethanol and isopropanol to afford 5-((9H-purin-6-yl)amino)isoindolin-1-one (Cpd. No. 1F) as off-white solid. Yield: 0.15 g, 58percent; MS (ESI) m/z 267 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 8.66 (s, 2H), 8.44 (s, 1H), 8.31 (d, J=1.9 Hz, 1H), 7.99 (dd, J=8.3, 1.8 Hz, 1H), 7.67 (d, J=8.3 Hz, 1H), 4.40 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 222036-66-0, its application will become more common.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-one, 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 222036-66-0, COA of Formula: C8H8N2O

A mixture of 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (100 mg, 0.26 mmol), 5-aminoisoindolin-1-one (38 mg, 0.26 mmol), 1-methyl-1H-imidazole (84 mg, 1.02 mmol) and EDCI (196 mg, 1.02 mmol) in DMF (3 mL) was stirred for 16 h at room temperature. Ethyl acetate (5 mL) and water (5 mL) were added. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (20 mL). The organic phases were combined and washed with brine (10 mL) then dried over Na2SO4. The residue was concentrated and triturated with MeOH (2 mL) to give 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)-N-(1-oxoisoindolin-5-yl)benzamide (26 mg, 20percent) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 10.68 (s, 1H), 9.97 (s, 1H), 8.61 (s, 1H), 8.52 (s, 1H), 8.44 (s, 1H), 8.24-8.08 (m, 4 h), 7.82-7.64 (m, 4 h), 7.41 (d, 1H, J=8.7 Hz), 7.11 (d, 1H, J=8.4 Hz), 4.39 (s, 2H), 4.02 (s, 3H), 3.76 (s, 3H). LC-MS: [M+H]+, 521.9, tR=1.434 min, HPLC: 96.12percent at 214 nm, 96.79percent at 254 nm, tR=3.673 min.

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; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 222036-66-0, name is 5-Aminoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 222036-66-0

Example 461-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(1-oxoisoindolin-5-yl)piperidine-3-carboxamideProcedure:To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (70 mg, 0.17 mmol) and 5-aminoisoindolin-1-one (25 mg, 0.17 mmol) in dichloromethane (15 mL) were added the solution of 1-methyl-1H-imidazole (55 mg, 0.68 mmol) and EDCI (129 mg, 0.68 mmol) in dichloromethane (5 mL), the reaction mixture was stirred at room temperature for 24 hours, the solvent was removed in vacuo, then methanol (5 mL) was added, the precipitate was collected by filtration and washed with methanol (3 mL) to afford 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(1-oxoisoindolin-5-yl)piperidine-3-carboxamide (48 mg, 51.8percent) as a brown solid. 1H NMR (300 MHz, DMSO): delta 10.29 (s, 1H), 9.64 (s, 1H), 8.84 (s, 1H), 8.38 (s, 1H), 7.96 (s, 1H), 7.64-7.53 (m, 3H), 7.33 (dd, 1H, J1=8.4 Hz, J2=1.8 Hz), 6.80 (brs, 1H), 4.81-4.63 (m, 2H), 4.33 (s, 2H), 3.68 (s, 3H), 3.59 (s, 3H), 3.14-2.92 (m, 2H), 2.65-2.60 (m, 1H), 2.04-2.00 (m, 1H), 1.81-1.69 (m, 2H), 1.49-1.45 (m, 1H). LC-MS: 545.9 [M+H]+, tR=1.42 min. HPLC: 99.69percent at 214 nm, 99.44percent at 254 nm, tR=4.87 min.

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; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-one, 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. category: indolines-derivatives

The 5-amino-isoindoline-one (Intermediate 8a, 2.1g, 14.2mmoL), acetone (3.5mL, 47.6mmoL) and sodium cyanide (2.1g, 46.8mmoL) was added to 90percent acetic acid (45mL) in.The addition was complete, stirred at room temperature for 48 hours.To the reaction mixture was added water (50mL) and ethyl acetate (100 mL), separated, the organic phase was washed with water (3 × 50 mL), saturated sodium bicarbonate (50 mL), water (50mL), dried over anhydrous magnesium sulfate , filtered, and the solvent was distilled off under reduced pressure, the residue was purified by flash column chromatography, eluent PE: EA = 1: 1, to give a white solid 2.7g, 88percent yield.

The synthetic route of 5-Aminoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-one, 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 222036-66-0, SDS of cas: 222036-66-0

A mixture of 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[l ,2-b]pyridazin-6-yl)benzoic acid (100 mg, 0.26 mmol), 5-aminoisoindolin-l-one (38 mg, 0.26 mmol), 1 -methyl- lH-imidzole (84 mg, 1.02 mmol) and EDCI (196 mg, 1.02 mmol) in DMF (3 mL) was stirred for 16 h at room temperature. Ethyl acetate (5 mL) and water (5 mL) were added. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (20 mL). The organic phases were combined and washed with brine (10 mL) then dried over Na2S04. The residue was concentrated and triturated with MeOH (2 mL) to give 3-(8-(5,6-dimethoxypyridin-2-ylamino) imidazo[l ,2- b]pyridazin-6-yl)-N-(l-oxoisoindolin-5-yl)benzamide (26 mg, 20 percent) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 10.68 (s, 1H), 9.97 (s, 1H), 8.61 (s, 1H), 8.52 (s, 1H), 8.44 (s, 1H), 8.24 – 8.08 (m, 4 h), 7.82 – 7.64 (m, 4 h), 7.41 (d, 1H, J = 8.7 Hz), 7.1 1 (d, 1H, J = 8.4 Hz), 4.39 (s, 2H), 4.02 (s, 3H), 3.76 (s, 3H). LC-MS : [M+H]+, 521.9, tR = 1.434 min, HPLC: 96.12 percent at 214nm, 96.79 percent at 254nm, tR = 3.673 min.

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; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 222036-66-0, name is 5-Aminoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 222036-66-0

A mixture of 5-aminoisoindolin-1-one (50mg, 0.34mmol), the compound id (172mg, 0.5 lmmol), p-toluenesulfonic acid (96mg, 0.5 lmmol), and n-BuOH (5mL) was stirred at 70°C for3 hours. The mixture was cooled and concentrated under reduced pressure; the residue was20 purified by Pre-TLC to afford the compound 8 as yellow solid (25mg, 16percent). MS: 45 1(M+H).H-NMR (DMSO-d6, 400MHz): oe 11.18 (s, 1H), 9.98 (s, 1H), 8.92 (s, 1H), 8.40 (s, 1H), 8.02 (s, 1H), 7.57-7.79 (m, 4H), 7.30 (t, 1H), 4.30 (s, 2H), 3.00 (s, 3H), 2.90 (s, 3H).

The synthetic route of 222036-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; ZHOU, Wenlai; LI, Runze; GAO, Panliang; WU, Xinping; BAI, Jinlong; YANG, Guiqun; WANG, Yanping; KANG, Di; (84 pag.)WO2018/19252; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem