Category: 2436-29-5

We’ll be discussing some of the latest developments in chemical about CAS: 2436-29-5. 2436-29-5

Intermediate 62 : 2-f3-f4-Methyl-3-oxopiperazin-l-vnpropynisoindoline-l,3- dione (0595) To a mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (515 mg, 2.53 mmol, commercially available from Fluorochem) and Na(OAc)3BH (815.9 mg, 3.85 mmol) in 2-MeTHF (20 mL) was added l-methylpiperazin-2-one (0.420 mL, 3.82 mmol, commercially available from Fluorochem). The mixture was stirred at rt for 4 h 45 min. To the reaction mixture was added aqueous 2M Na2C03 (10 mL) and this mixture stirred at rt for 10 min giving an aqueous phase at approximately pH 10. The layers were separated and the aqueous layer washed with EtOAc (2 x 10 mL). The organic layers were filtered through a cartridge fitted with a hydrophobic frit and the filtrate evaporated in vacuo to give a pale yellow crystalline solid. 2-(3-(4-methyl-3-oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (660.5 mg, 2.192 mmol, 86 % yield). (0596) LCMS (2 min high pH); Rt = 0.74 min, m/z = 302 for [MH]+

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Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
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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. 2436-29-5

Step 5. 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione To a solution of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-amine 15 (31 mg, 1 eq.) in CH2Cl2 (3 ml), was added aldehyde 16 (0.8 eq., 17 mg), sodium triacetoxy borohydride, and acetic acid. The reaction mixture was stirred for 3 h at room temperature. Water was added and then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to yield 46 mg of 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 17.

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Reference:
Patent; Wang, Weibo; Constantine, Ryan N.; Lagniton, Liana Marie; Bair, Kenneth; US2005/261337; (2005); A1;,
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Electric Literature 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.

Into a heat-vacuum dried 50 mL recovery flask, DMF (13 mL), 3-phthalimidylpropanal (manufactured by Aurora Fine Chemicals, 266.0 mg, 1.13 mmol, 1 equivalent), N,N-diallylthioacetamide (244 muL, 1.35 mmol, 1.2 equivalents), and the Cu/(S,S)-Ph-BPE solution prepared as above (100 muL, 0.10 mmol, 0.09 equivalent) were added under an argon atmosphere. The recovery flask was transferred to a constant temperature bath of -40C, and the THF solution of 2,2,5,7,8-pentamethylchromanol lithium salt prepared as above (50 muL, 0.10 mmol, 0.09 equivalent) was added, followed by stirring at -40C for 24 hours. Subsequently, a saturated aqueous solution of ammonium chloride (5 mL) and 2,2-bipyridine (15.6 mg, 0.10 mmol, 0.09 equivalent) were added, and the resulting mixture was extracted three times with ethyl acetate (5 mL). The resulting organic layer was sequentially washed with distilled water, saturated sodium bicarbonate water, and saturated brine, and then dried over anhydrous sodium sulphate. After filtration and concentration, the residue thus obtained was purified by flash column chromatography (hexane/ethyl acetate = 7/1 to 2/1 (volume ratio)) to obtain the following thioamide compound A-4 as a yellow oily matter. Yield 251.1 mg (62%, 75%ee).

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:
Patent; Microbial Chemistry Research Foundation; SHIBASAKI, Masakatsu; KUMAGAI, Naoya; EP2679580; (2014); A1;,
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Related Products of 2436-29-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, This compound has unique chemical properties. The synthetic route is as follows.

Example 26Synthesis of 2-(3-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)propyl)isoindoline-1,3-dione (181) To a slurry of 4-(4-amino-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine (150 mg, 0.42 mmol) in 1,2-dichloromethane (10 ml) was added N,N-diisopropylethylamine (250 mul) followed by acetic acid (0.5 ml), 3-(1,3-dioxoisoindolin-2-yl)propanal (140 mg) and sodium triacetoxyborohydride (200 mg). The mixture was stirred at room temperature for 24 hours before being poured into ethyl acetate (100 ml) washed with water (250 ml) and dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow oil which was purified by silica gel chromatography eluting with 40-60% ethyl acetate in hexanes to yield 2-(3-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)propyl)isoindoline-1,3-dione 181 as a yellow foam (95 mg). 1H NMR (CDCl3) 400 MHz delta 8.34 (d, J=5.2 Hz, 1H), 7.87 (s, 1H), 7.86-7.83 (m, 3H), 7.8 (d, J=8.8 Hz, 1H), 7.75-7.71 (m, 2H), 7.34 (s, 1H), 7.31 (d, J=2.4 Hz, 1H), 7.18 (dd, J=2.4 and 8.8 Hz, 1H), 7.08 (d, J=4.8 Hz, 1H), 5.24 (m, 1H), 4.9 (m, 1H), 4.04 (s, 3H), 3.9 (t, J=6.0 Hz 2H), 3.5 (t, J=6.0 Hz, 2H), 3.11 (d, J=5.2 Hz, 3H), 2.24 (m, 2H), 2.2-2.14 (m, 2H), LCMS m/e 468 (M+H)

The chemical industry reduces the impact on the environment during synthesis 3-(1,3-Dioxoisoindolin-2-yl)propanal. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ArQule, Inc.; US2011/166137; (2011); A1;,
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Indoline | C8H9N – PubChem

Related Products 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.

ally:3L reaction flask was added dichloromethane 800mL, Et2NH (175.5mL, 1.68mol, 2.1eq), K2CO3 (121.6g, 0.88mol, 1.1eq), a mechanical stirrer, nitrogen atmosphere, was cooled to 0 deg.] C, was added dropwise over 25 minutes 3- [2- (1,3-diketo isoindoline)] propanal (162.55g, 0.80mol, 1.0eq) dissolved in 800mL DCM solution was added dropwise to 0 stirred for 5 minutes, then at room temperature for 3 hours.After concentrating the solvent was filtered off portion, the filtrate was concentrated dryness to give 199.93g crude D2, crude yield: 97%.(Instability resulting intermediate, required stored at -20 ).

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

Reference:
Patent; Jie Da Wei (Shanghai) Pharmaceutical Technology Development Co., Ltd; Tang, Yanlin; Chen, Keshi; (10 pag.)CN105906569; (2016); A;,
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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.

3-(1,3-Dioxoisoindolin-2-yl)propanal (2.5 g, 12.3 mmol) was dissolved in 80 mL of DCM. (1ethoxycarbonylethylidene)triphenylphosphorane (4.50 g, 12.9 mmol) was added thereto, and the mixtue was stirred at room temperaturefor 2 hours. The reaction solution was concentrated under reduced pressure and purified by column chromatography toobtain the title compound (2.99 g, 89 %).1H-NMR (CDCl3) delta7.83 (2H, m), 7.72 (2H, m), 6.91 (1H, m), 5.90 (1H, d), 4.16 (2H, q), 3.83 (2H, t), 2.60 (2H, m), 1.26 (3H, t)

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

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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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., Formula: C11H9NO3

A solution of 7a (30.1 mg, 0.15 mmol, 1.5 eq) and (S)-10 (0.6 mg, 0.001 mmol, 0.01 eq) was stirred atroom temperature in anhydrous THF (2 mL) for 30 min before adding NFSI (31.2 mg, 0.01 mmol,1 eq). The reaction mixture was then stirred at room temperature for 6 h, then pentane was added andthe precipitate was filtered off. The residue was concentrated and then dissolved in MeOH (2 mL),NaBH4 (1 mmol) was added and stirred for 1 h at room temperature. The reaction was quenched with(1M, 2 mL) aqueous solution of KHSO4, (2 mL) water was added and the aqueous layer was extractedwith EtOAc (3 5 mL), the organic layers was collected and dried over MgSO4 and evaporated invacuo. The crude compound was subjected to silica gel column (98%-90% hexane/EtOAc) to give thetitle compound as colourless oil;

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; Cheerlavancha, Raju; Ahmed, Ahmed; Leung, Yun Cheuk; Lawer, Aggie; Liu, Qing-Quan; Cagnes, Marina; Jang, Hee-Chan; Hu, Xiang-Guo; Hunter, Luke; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2316 – 2325;,
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Synthetic Route 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.

Step 1.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 (400 mg, 1.3 mmol) and 3-(l,3-dioxoisoindolin-2- yl)propanal (293 mg, crude 1.44mmol) in DCE (8 mL) were stirred at rt for 0.5 h, then NaBH(OAc)3 (416 mg, 1.96 mmol) was added. The reaction was stirred at rt overnight. The reaction was quenched with aqu. sat. NaHC03 (2 mL), extracted with DCM (10 mLx3), washed with brine (10 mL), dried and concentrated. The residue was purified by prep-TLC (DCM : MeOH = 10 : 1) to the title compound (350 mg, Yield 43%). NMR (500 MHz, MeOD): delta 8.28 (s, 1H), 8.21 (s, 1H), 7.83-7.76 (m, 4H), 6.14(d, J = 3.5 Hz, 1H), 5.46-5.44 (m, 1H ), 5.01-4.99 (m, 1H), 4.32 (br s, 1H), 3.65-3.62 (m, 2H), 2.85-2.83 (m, 2H), 2.57-2.53 (m, 2H), 1.79-1.76 (m, 2H), 1.58 (s, 3H), 1.37 (s, 3H) ppm; ESI-MS (m/z): 494.2[M+1]+.

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, 3-(1,3-Dioxoisoindolin-2-yl)propanal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Formula: C11H9NO3

In a 10 ml reaction tube, adding phosphine nitrogen ligand L10a (0.35 mg, 0 . 65 mumol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 mumol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding beta – aminoketone laq (40.6 mg, 0.2 mmol) with anhydrous sodium carbonate (2.12 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 aq. The conversion is 100%, enantiomeric excess is 92%. 2 Aq: white solid. According to the embodiment 1 – 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2436-29-5, its application will become more common.

Reference:
Patent; Shanghai Jiao Tong University; Shanghai Zizhu Rising Industrial Technology Institute; Zhang Wanbin; Liu Delong; Wang Yanzhao; Jiang Xiuchen; Cao Lingyu; (32 pag.)CN105085372; (2018); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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 mixture of (R)-(l-amino-but-3-ynyl)-7-chloro-3-phenylamino-3H-quinazolin-4-one (4.60 g, 12.2 mmol) and diisopropylethylamine (DIPEA) (5.5 ml) in dichloromethane (60 ml) was added a solution of 3-(l,3-dioxo-l,3-dihydro-isoindol-2-yl)-propionaldehyde (2.45 g, 12.1 mmol) in dichloroethane (10 ml), followed by a solution of sodium triacetoxy borohydride (NaBH(OAc)3) (0.25M in dichloroethane, 100 ml). The reaction mixture was stirred at room temperature and the reaction progress was monitored by HPLC/MS. Upon completion, a saturated sodium carbonate solution (100 ml) was added. The resulted organic layer was collected and washed with brine solution. The solvent was removed and residue was purified by flash column to afford 2- {3-[(R)- 1 -(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3- ynylamino]-propyl}-isoindole-l,3-dione (6.1 g, 95%) as off-white solid. M.p. 78-80 0C. LCMS: m/e 526 [M+H]. 1H NMR (DMSO-d6): delta 9.09 (s, br, IH), 8.07 (d, J= 8.8 Hz, IH), 7.74 (m, IH), 7.83-7.76 (m, 5H), 7.58 (dd, J= 8.8 and 2.0 Hz, IH), 7.17 (t, J= 7.6 Hz, 2H), 6.83 (brm, IH), 6.65 (m, 2H), 4.1 and 4.0 (s,s, br, IH, rotomers), 3.6 (t, J= 6.8Hz, 2H), 2.75 (s, br, 1 H), 2.67- 2.52 (brm, 2H), 2.35 (brm, 2H), 1.67 (brm, 2H).

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

Reference:
Patent; ARQULE, INC.; WO2009/2808; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem