Category: 2436-29-5

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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., Computed Properties of C11H9NO3

Compound 359l-(3-((((2R^S,4R,5R)-5 6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyl)(isopropyl)amino)propyl)-3-(3-chlorophenyl)ureaStep 1. Preparation of 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)methyl)amino)propyl)isoindoline-l,3- dioneTo a solution of 2-(3-hydroxypropyl)isoindoline-l,3-dione (1.0 g, 4.88 mmol) in EA (50 mL) was added IBX (3.4 g, 12.19 mmol). The mixture was heated to reflux for 2h. After cooling, the mixture was filtered and the filtrate was concentrated to give 3-(l,3- dioxoisoindolin-2-yl)propanal crude (not weight), which was directly used for next step.To a solution of 9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)-9H-purin-6-amine (1.5 g, 4.90 mmol) and 3- (l ,3-dioxoisoindolin-2-yl)propanal (from last step) in DCE (50 mL) was added NaBH(OAc)3 (1.56 g, 7.30 mmol). The reaction mixture was stirred at rt overnight then saturated NaHC03 aqueous solution (50 mL) was added. The resulting mixture was extracted with DCM (50 mL x 2). The combined organic layers were dried over Na2S04 and concentrated. The residue was purified by SGC (DCM : MeOH = 100 : 1 to 10 : 1) to afford the title compound (1.38 g, yield: 57%) as a white solid. 1H NMR (500 MHz, MeOD): 58.30 (s, 1H), 8.23 (s, 1H), 7.85-7.79 (m, 4H), 6.17 (d, J = 2.5 Hz, 1H), 5.48 (dd, J = 2.5, 6.0 Hz, 1H), 5.03 (dd, J = 3.0, 6.5 Hz, 1H), 4.36 (t , J = 3.5 Hz, 1H), 3.67-3.65 (m, 2H), 2.94-2.89 (m, 2H), 2.62-2.60 (m, 2H), 1.82-1.79 (m, 2H), 1.60 (s, 9H), 1.39 (s, 3H) ppm; ESI-MS (m/z): 494.2 [M+l]+.

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; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., name: 3-(1,3-Dioxoisoindolin-2-yl)propanal

Example M9 N-(3-Aminopropyl)-N-{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}-2-hydroxyacetamide 150.0 mg (0.42 mmol) of (1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropan-1-amine (Intermediate C52) were initially charged in 2.0 ml of dichloromethane, and 29.2 mg (0.49 mmol) of HOAc and 125.6 mg (0.59 mmol) of sodium triacetoxyborohydride were added and the mixture was stirred at RT for 5 min. 98.9 mg (0.49 mmol) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal were added. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and the organic phase was washed twice with saturated sodium carbonate solution and once with saturated NaCl solution. After drying over magnesium sulphate, the solvent was evaporated under reduced pressure and the residue was purified on silica gel (eluent: dichloromethane/methanol 100:1). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 188.6 mg (74%) of the compound 2-[3-({(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}amino)propyl]-1H-isoindole-1,3(2H)-dione. LC-MS (Method 1): Rt=1.00 min; MS (ESIpos): m/z=541 [M+H]+.

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; MARX, Leo; JOHANNES, Sarah Anna Liesa; STELTE-LUDWIG, Beatrix; DIETZ, Lisa; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (481 pag.)US2019/77752; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 a solution of 4b (1.00 g, 3.63 mmol) and 7b (1.11 g, 5.45 mmol) in THF (35 mL) was added NH4OAc (2.80 g, 36.3 mmol) in MeOH (35 mL). The reaction mixture was stirred at reflux temperature for 2 h and concentrated. The residue was diluted in CHCl3 and washed with a saturated aqueous solution of Na2CO3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-5% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow amorphous (1.14 g, 69%): 1H NMR (200 MHz, CDCl3, delta): 2.42 (d, J = 0.7 Hz, 3H), 3.22 (t, J = 6.8 Hz, 2H), 4.15 (t, J = 6.8 Hz, 2H), 6.00 (s, 2H), 6.69 (s, 1H), 6.85 (d, J = 8.1 Hz, 1H), 7.09 – 7.35 (m, 2H), 7.69 – 7.87 (m, 4 H); MS (ESI) m/z 459 [M+H]+, 35%, 481 [M+Na]+, 100%, 457 [M-H]-, 100%. To a suspension of 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (1.12 g, 2.43 mmol) in EtOH (60 mL) was added hydrazine monohydrate (1.18 mL, 24.3 mmol). The reaction mixture was stirred at reflux temperature for 8 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by column chromatography on NH-silica gel eluting with 2-7% MeOH/CHCl3 to afford 8b as a pale yellow amorphous (567 mg, 71%): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.9 Hz, 3 H), 2.91 (t, J = 5.9 Hz, 2 H), 3.18 (t, J = 5.9 Hz, 2 H), 6.00 (s, 2 H), 6.70 (d, J = 0.9 Hz, 1 H), 6.86 (d, J = 8.1 Hz, 1 H), 7.24 (dd J = 8.1, 1.7 Hz, 1 H), 7.36 (d, J = 1.7 Hz, 1 H); MS (ESI) m/z 329 [M+H]+, 90%, 351 [M+Na]+, 100%, 327 [M-H]-, 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

B] Preparation of compound 1-B; 0.38 g (0.99 mmol) of compound 1-A is dissolved in 15 ml methanol and 0.26 g (1.28 mmol) of 3-(l,3-dioxo-l,3-dihydroisoindol-2-yl)-propionaldehyde, 0.1 ml acetic acid and 0.125 g (1.98 mmol) OfNaBH3CN are added to the solution. The mixture is stirred at 28C for 3.5 hours and the solvent is subsequently evaporated. The crude product is purified by column chromatography on silica gel (petroleum ether(ethyl acetate 10:1 -> 5:1) to give 380 mg (65%) of the desired product as a light yellow solid.

The synthetic route of 3-(1,3-Dioxoisoindolin-2-yl)propanal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; KELLENBERGER, Johannes, Laurenz; DREIER, Juerg; WO2011/18510; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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. SDS of cas: 2436-29-5

Bromine (0.22 ml, 4.29 mmol) was added dropwise to a solution (30 ml) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal (866 mg, 4.36 mmol) in acetic acid at room temperature. After stirring at room temperature for 2 hours, the reaction solution changed in color from brown to colorless. Thiourea (373 mg, 4.90 mmol) was added to the reaction solution and the resulting mixture was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with methanol-diethyl ether and then dried. The solvent was distilled off under reduced pressure to obtain the title compound (616 mg, 55.8%).; LC/MS (M+1, retention time): 260.0, 3.76 min.

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1640369; (2006); 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., Product Details of 2436-29-5

Synthesis of Compound 42; A solution of 0.200 g (0.26 mmol) of 41,0. 262 g (1.29 mmol) of 3- (N-phthalimidyl)- propionaldehyde, and 0.110 g (0.52 mmol) of NaB (OAc) 3H in 1.5 mL of DMF was stirred at 25 C for 4 h. The reaction mixture was diluted with H20, extracted with CH2C12 (50 mL x 3), combined organic layers were washed with brine, dried over MgS04, concentrated, purified through silica gel column chromatography to give 0.200 g of product. MS (ESI) nVe 961 (M+H) Synthesis of triazole 460 A solution of 0.200 g (0.20 mmol) of alkyne 42,0. 080 g (0.41 mmol) of azide 14w, and 0.040 g (0.20 mmol) of Cul in 15 mL of THF was degassed, then put under argon. To it was added 0.2 mL of Hunig’s base. The reaction was stirred at 25 C for 6 h. Subsequently, to the mixture was added 40 rnL of 10% NH40H, stirred for 10 min, extracted with CH2C12 (50 ml x 3), the combined organic layers were washed with brine, dried, concentrated, purified by preparative TLC to give 0.098 g of compound 460. MS (ESI) iiz/e 1153 (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; RIB-X PHARMACEUTICALS, INC.; WO2005/85266; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2436-29-5, 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 2436-29-5 as follows.

A solution of N-chloro-3-phenylaniline (1.00 g, 4.91 mmol) in ethylene dichloride (10.0 mL) was cooled to 0 C and treated with 3-(1,3-dioxoisoindolin-2-yl)propanal (1.05 g, 5.15 mmol) and sodium triacetoxyborohydride (1.46 g, 6.87 mmol). The mixture was warmed to 25 C and stirred for 24 h. The mixture was treated with a solution of 1 M aqueous NaOH (2.0 mL), stirred for 0.5 h, then partitioned between between saturated aqueous NaCl (100 mL), and CH2Cl2 (100 mL). The organic layer was washed with saturated aqueous NaCl (3 100 mL), dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in a minimal amount of CH2Cl2 and purified by flash chromatography (SiO2, 0-10% ethyl acetate-hexanes) to afford the title compound as a yellow oil (0.847 g, 44%). 1H NMR (600 MHz, CDCl3) 7.84 (2H, dd, J = 5.4, 3.1 Hz), 7.72 (2H, dd, J = 5.5, 3.0 Hz), 7.32 (2H, t, J = 7.9 Hz), 7.07-7.12 (4H, m), 6.78 (2H, m), 6.71 (1H, m), 3.78 (4H, m), 2.06 (2H, quintet, J = 7.5 Hz); 13C NMR (150 MHz, CDCl3) 168.5, 149.5, 146.9, 135.1, 134.2, 132.2, 130.3, 129.9, 124.5, 124.1, 123.5, 119.8, 118.0, 116.2, 50.1, 36.1, 27.0; LCMS m/z 391.1 ([M + H+], C23H19ClN2O2 requires 391.1).

According to the analysis of related databases, 2436-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kastrinsky, David B.; Sangodkar, Jaya; Zaware, Nilesh; Izadmehr, Sudeh; Dhawan, Neil S.; Narla, Goutham; Ohlmeyer, Michael; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6528 – 6534;,
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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H9NO3

General procedure: Neat TiCl4 (120 muL, 1.1 mmol) was added dropwise to a solution of the corresponding alpha-silyloxy methyl ketone (1.0 mmol) in CH2Cl2 (5.0 mL) at -94 C, and the mixture was stirred for 5 min. Then, anhydrous i-Pr2NEt (190 muL, 1.1 mmol) was added dropwise and the resulting dark red solution was stirred for 30 min at -94 C. After dropwise addition of the freshly distilled aldehyde (1.5 mmol), stirring was continued for 30 min at -78 C. The reaction was quenched by the addition of saturated NH4Cl (5 mL) and vigorously stirred at room temperature for 10 min. Then it was diluted with Et2O (50 mL), and washed with H2O (50 mL), saturated NaHCO3 (50 mL) and brine (50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The resulting crude was analysed by 1H NMR and purified by column chromatography.

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; Lorente, Adriana; Pellicena, Miquel; Romea, Pedro; Urpi, Felix; Tetrahedron; vol. 71; 7; (2015); p. 1023 – 1035;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 2436-29-5 as follows. COA of Formula: C11H9NO3

Step 11. 2-(3-{[1-(3-Benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione; The product from Step 10 (20), 42 mg (0.13 mmol) was dissolved in anhydrous CH2Cl2 followed by the addition of phthalimide protected 3-aminopropionaldehyde 33 mg (0.16 mmol) and 37 mg (0.18 mmol) of sodium acetoxyborohydride and finally 10 mul (0.18 mmol) of acetic acid. The reaction was left stirring at room temperature for 2.5 h. The solvent was evaporated and the product redissolved in ethyl acetate and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated and dried under high vacuum resulting in 63 mg (0.13 mmol, 94%) of 2-(3-{[1-(3-benzyl-4-oxo-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (21) as a white solid.

According to the analysis of related databases, 2436-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiron Corporation; US2005/228002; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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 2436-29-5, Computed Properties of C11H9NO3

150.0 mg (0.42 mmol) of (1 R)- 1- [1 -benzyl-4-(2,5-difluorophenyl)- I H-pyrrol-2-yl] -2,2-dimethyipropan-1-amine (intermediate C52) were initially charged in 2.0 ml of dichloromethane, and 29.2 mg (0.49mmol) of HOAc and 125.6 mg (0.59 mmol) of sodium triacetoxyborohydride were added and the mixture was stirred at RI for 5 mm. 98.9 mg (0.49 mmol) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2- yl)propanal were added. Ihe reaction mixture was stirred at RI overnight. Ihe reaction mixture was then diluted with ethyl acetate and the organic phase was washed twice with saturated sodium carbonate solution and once with saturated NaC1 solution. After drying over magnesium sulphate, the solvent wasevaporated under reduced pressure and the residue was purified using silica gel (mobile phase:dichloromethane/methanol 100:1). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. Ihis gave 188.6 mg (74%) of the compound 2-[3-({(1R)-1-[1-benzyl-4- (2,5-difluorophenyl)- 1 H-pyrrol-2-yl] -2,2-dimethylpropyl} amino)propyl] -1 H-isoindole- I ,3(2H)-dione.LC-MS (Method 1): R1 = 1.00 mm; MS (ESIpos): mz = 541 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(1,3-Dioxoisoindolin-2-yl)propanal, and friends who are interested can also refer to it.