Category: 675109-45-2

Some common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-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. COA of Formula: C8H8N2O

To ethyl acetate (10 mL) was added 6-aminoisoindolin-l-one (100 mg, 0.675 mmol), (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (179 mg, 0.675 mmol), and DCC (209 mg, 1.012 mmol). The reaction mixture was stirred for 24 h, diluted with ethyl acetate and filtered. The filtrate was washed with 10% citric acid (1 x 10 mL), brine and dried (MgSO4). The crude product was purified by silica gel chromatography (DCM and 0-10%MeOH as eluents) to afford a white foam (0.192 g). The foam was re-dissolved in DCM (5 mL) and to this solution was added TFA (2 mL). After 1 h, the reaction was concentrated to afford 129A (0.29 g, 105%) as a brown oil. LCMS m/z 296.3 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-45-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/157162; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 675109-45-2, A common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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 Intermediate 6 (0.1 g, 0.675 mmol) and 4-fluoro-3- methoxyphenylboronic acid (0.115 g, 0.675 mmol) in acetonitrile (1.8 mL) and DMF (0.50 mL) was added 2-oxoacetic acid (0.062 g, 0.675 mmol). The reaction was mixture was sonicated for 5 minutes and heated to 90 0C for 20 min on a biotage microwave. The solvent was concentrated and the crude product was dissolved in a small amount of chloroform and charged to a 40 g silica gel cartridge which was eluted with a 40 min gradient time from 0-20% methanol / dichloromethane. The product peak was isolated and dried to give 24A (0.086 g, 39%) brown solid product. 1H NMR (400 MHz, methanol-d4) delta ppm 3.82 – 3.88 (m, 3 H) 4.25 – 4.31 (m, 2 H) 5.10 (s, 1 H) 6.88 – 7.01 (m, 2 H) 7.02 – 7.13 (m, 2 H) 7.23 – 7.32 (m, 2 H); MS (ESI)(m/z) 331.3 [M+H]+ .

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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-45-2, 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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

6-Ammnoisoindolin-1-one (15.34 mg, 0.104 mmol) was dissolved in DCM (1.0 mL) along with pyridine (0.039 mL, 0.487 mmol) and DIEA (0.032 mL, 0.183 mmol). Intermediate 14SF (28 mg, 0.061 mmol) in 2 mL of DCM was added dropwise, and the reaction mixture was stirred at room temperature for 50 minutes. The reaction was quenched with 1.0 N HC1 (0.5 mL). All solvent was removed under vacuum. The crudewas dissolved in DMSO/THF (2:1, 6 mL) and purified via preparative LC/MS (method C,40-100% B over 18 mm, then a 5-mm hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to yield Example 178 (10.7 mg, 31% yield). ?H NMR (500MHz, DMSO-d6) 8.72 (s, 1H), 8.56 (s, 1H), 8.51 (br. s., 1H), 7.86 (d, J=10.7 Hz, 2H), 7.81 (br. s., 2H), 7.61 (br. s., 1H), 7.46 (d, J=5.8 Hz, 1H),5.48-5.38 (m, 1H), 4.54 (d, J12.2 Hz, 1H), 4.41 (dd, J=12. 1, 7.2 Hz, 1H), 4.29 (s, 2H),4.08 (s, 3H), 3.64 (dd, J15.9, 9.8 Hz, 1H), 3.36 (d, J=13.7 Hz, 1H), 2.62 (s, 3H);LC-MS: method C, 2 to 98% B. RT = 2.21 mm, MS (ESI) m/z: 572.30 (M+H).Analytical HPLC purity (method B): 100%.

The synthetic route of 6-Amino-2,3-dihydro-1H-isoindol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); 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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, A new synthetic method of this compound is introduced below., Product Details of 675109-45-2

To a toluene solution (5 mL) of compound Int-1 (100 mg), m-CPBA (146 mg) was added and stirred at room temperature overnight to obtain a solution A. NaH (56 mg) was added to a DMF (5 mL) solution in which Compound A-31 (54 mg) was dissolved, and stirred at room temperature for 30 minutes to obtain a mixture B. Then A was slowly added to B and stirred overnight at room temperature. The reaction solution was poured into a saturated ammonium chloride solution, a white solid was precipitated, and the filter cake was purified by thin layer chromatography TLC (dichloromethane: methanol (v / v) = 20: 1) to obtain a crude product. Methanol (2 mL) was added, and then placed in an ultrasonic cleaner for 5 minutes, filtered, and the filter cake was dried to obtain the standard product HY-B030 (5.8 mg) as a white solid.

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; Shanghai Hongyi Biological Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Wu Rongguang; Li Jia; Yi Dewu; Zhou Yubo; Ye Wei; Wang Peipei; Xiang Junfeng; Zhang Kaixiang; Hu Xiaobei; (61 pag.)CN110872296; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem