Tag: M.W=300-400

Electric Literature of 35197-64-9, 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 35197-64-9 as follows.

General procedure: In this work, previously reported N-benzyl-2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanamide derivatives (25a-e) [44] were obtained by activating the carboxylic acid group of 24 (1 eqv) by using n-propanephosphonic acid anhydride (T3P, 50% in EtOAc, 1 eqv). The reaction was carried out under argon atmosphere for 2hat 0C in dry methylene chloride. Then, distilled triethylamine (1.2 eqv) and the appropriate N-benzylamine (1.1 eqv) were added to the reaction mixture [57]. The reaction was continued at room temperature for 12h. The products were purified by column chromatography over silica gel (DCM/acetone=9:1) to yield 25a-e as a white solid.

According to the analysis of related databases, 35197-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; ?mudzki, Pawe?; Fija?kowski, ?ukasz; Furga?a, Anna; Gryz?o, Beata; Hoefner, Georg C.; Kulig, Katarzyna; Malawska, Barbara; Malawska, Katarzyna; Nowaczyk, Alicja; Podkowa, Adrian; Rapacz, Anna; Sa?at, Kinga; Wanner, Klaus T.; Zar?ba, Paula; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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Synthetic Route of 1201923-48-9, 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. 1201923-48-9 name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, 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.

To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 ml.) at RT was added 4M HCI in dioxane (56 ml_, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 ml.) affording the title compound (7.8 g,99%) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLIKE BEECHAM CORPORATION; WO2009/158371; (2009); A1;,
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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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid

Ethyl 2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanoate (17, n=2):5 Thionyl chloride (3.1 mL, 4-5 eq) was dissolved in CCl4. Then Pht-GABA (2.4 g, 10.3 mmol) was added. The slurry was put on oil bath at ~85 oC and refluxed for 1 h 15 min. Everything dissolved within a few minutes. NBS (1.2 eq., 12.36 mmol, 2.2 g) was added to the warm solution forming yellow slurry. On addition of 3 drops of 40% HBr(aq) everything dissolved and solution became red. Reaction mixture was heated under reflux. Within 1 h of reflux in homogenous mixture turned black. After additional 10 min reaction mixture was cooled down, poured into 15 mL of dry EtOH (exothermic), followed by addition of EtOH (2×15 mL). After 10 min it was evaporated to dryness. Product isolated using column chromatography

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 35197-64-9.

Reference:
Article; Coxon, Fraser; Joachimiak, ?ukasz; Najumudeen, Arafath Kaja; Breen, George; Gmach, Joanna; Oetken-Lindholm, Christina; Way, Rebecca; Dunford, James; Abankwa, Daniel; B?azewska, Katarzyna M.; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 77 – 89;,
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17702-83-9, name is 2-(8-Bromooctyl)isoindoline-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. name: 2-(8-Bromooctyl)isoindoline-1,3-dione

2-(8-(6-Amino-8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-9H-purin-9-yl)octyl)isoindoline-1,3-dione (16c) (Scheme 4). 200 mg (0.484 mmol) of Compound 11 was dissolved in DMF (8 mL). 466 mg (1.43 mmol) of Cs2CO3 and 819 mg (2.42 mmol) N-(8-bromooctyl)phthalimide were added and the mixture was sonicated for 1.5 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (CH2Cl2:MeOH:AcOH, 15:1:0.5) to give 120 mg (34percent) of Compound 16c. 1H NMR (500 MHz, CDCl3) delta 8.29 (s, 1H), 7.84 (dd, J = 5.5, 3.1 Hz, 2H), 7.70 (dd, J = 5.5, 3.1 Hz, 2H), 7.28 (s, 1H), 6.87 (s, 1H), 6.29 (br s, 2H), 5.96 (s, 2H), 4.18 (t, J = 7.5 Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 1.62-1.77 (m, 4H), 1.25-1.36 (m, 8H); MS (ESI) m/z 671.3 [M+H]+.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sloan Kettering Institute For Cancer Research; Cornell University; CHIOSIS, Gabriela; PILLARSETTY, Nagavarakishore; LEWIS, Jason S.; LARSON, Steven M.; TALDONE, Tony; ALPAUGH, Mary L.; (168 pag.)EP3208615; (2017); A2;,
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Synthetic Route of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) Preparation of 8-(cis/trans-2,6-dimethyl)morpholinyloctyl phthalimide 8-Bromooctylphthalimide (9 g; 26.60 mmoles) and 2,6-dimethyl morpholine (cis-trans isomers mix) (9.8 ml; 79.5 mmoles) were dissolved in anhydrous acetonitrile (50 ml). The mixture was allowed to stir at room temperature for 18 hours approx. The reaction was discontinued by solvent evaporation under reduced pressure. The collected residue was purified by chromatography on silica gel (CH2 Cl2 /MeOH 95:5). The first product isolated (Rf =0.7) is a light yellow oil (A trans) (2.04 g), the second (Rf =0.4) is a yellow oil (B cis) (3.4 g). Total yield 54.8percent. Analysis: calcd.: C,70.93; H,8.66; N,7.52. Compound A (trans isomer) found: C,71.14; H,8.58; N,7.59. Compound B (cis isomer) found: C,71.07; H,8.53; N,7.65.

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, 2-(8-Bromooctyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mediolanum Farmaceutici S.p.A.; US5302593; (1994); A;,
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These common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-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. Product Details of 17702-83-9

b) Preparation of 8-morpholinyloctylphthalimide 8-Bromooctylphthalimide (676 mg; 2.0 mmoles) and morpholine (0.35 ml; 4.0 mmoles) were dissolved in anhydrous acetonitrile (5 ml). Reaction times and process as per Example 1. 331 mg of pure product were obtained. Yield 48percent.

The synthetic route of 2-(8-Bromooctyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); 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 24566-79-8 as follows. Computed Properties of C14H16BrNO2

To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassium thioacetate (2.78 g, 34.3 mmol) portion wise and stirred for 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 mL) and stirred for 1 h. The resultant precipitated was filtered, washed with water (100 mL) and dried in vacuo to afford 4-i as an off-white solid(5.8 g, 93.5%). LCMS: 306.20 (M+1).

According to the analysis of related databases, 24566-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (340 pag.)WO2018/98207; (2018); A1;,
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Electric Literature of 446292-07-5,Some common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, molecular formula is C21H21N3O5, 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.

100 g (i?)-2-(2-hydroxy-3-(4-(3-oxo-morpholino) phenyl amino) propyl) isoindoline-l,3-dione of Formula (F) and MDC (1000 ml) were added to RBF at 25C to 35C and heated to 40C to 45C. Further, 61 g Nu,Nu-Carbonyl diimidazole (CDI) and 0.5 g DMAP were added and stirred for 3-4 hours. Excess MDC was evaporated under reduced pressure. The reaction mass was cooled to 25C to 35C followed by addition of dilute HCl solution and stirred for 1 hour and finally filtered and washed with 2 x 200 ml water to afford title compound as (S)-2-((2-oxo 3-(4-(3-oxo- mo holno)phenyl)oxazolidin-5-yl)methyl)isoindoline-l,3-dione of Formula (I).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DWIVEDI, Shriprakash, Dhar; PRASAD, Ashok; PAL, Daya, Ram; SHARMA, Mukul, Hari, Prasad; JAIN, Kuldeep, Natwarlal; PATEL, Naitik, Bharatbhai; WO2013/98833; (2013); A2;,
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Some common heterocyclic compound, 105310-75-6, name is cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide, molecular formula is C23H24N2O3, 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. Product Details of 105310-75-6

In a round bottom flask, 450ml of 40% aqueous methylamine solution was charged and 1 OOg of compound of formula III, prepared as in Example 1 , was added at about room temperature. Then the temperature was raised to about 40C to about 45C and stirred for about 2h. The reaction mixture was cooled to about room temperature and 700ml of toluene was added and stirred for about 30min. The layers were separated and the aqueous layer was extracted twice with each 200ml of toluene. The organic layers were combined and washed with 200ml of water followed by washing with 100ml of 20% aqueous sodium chloride solution. The organic layer was distilled out under reduced pressure at about 50C to about 55C, until substantially all of the solvent was distilled out. The crude was cooled to about room temperature and 350ml of ethyl acetate was added and stirred the contents for about 15min. Then 5g of activated charcoal (5g of charcoal in 50ml of isopropanol) was added to the solution and stirred for about 30min at about room temperature. The solution was filtered through Hyflo bed and the Hyflo bed was washed with 50ml of ethylacetate. The solution was cooled to about 20C and 93g of 12% w/w hydrogen chloride solution in ethylacetate was added at about 20C to about 25C over a period of about 30min and the contents were stirred for about 2h at about 20C to about 25C. The precipitated product was filtered and washed with 100ml of ethylacetate. The product was dried at about 55C to about 60C under vacuum for about 6h to yield 50g of milnacipran hydrochloride.Purity by HPLC: 99.1%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105310-75-6, its application will become more common.

Reference:
Patent; GLENMARK GENERICS LIMITED; JAMBUKAR, Nagambar Genuji; GHARPURE, Milind; SINARE, Sudam Nanabhau; THOMBRE, Pravin Chhaburao; KHAN, Mubeen Ahmed; WO2011/158249; (2011); A1;,
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Related Products of 85342-65-0, 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. 85342-65-0, name is 4,5,6,7-Tetrachloro-2-hydroxyisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A screw-capped culture tube with a stir bar was charged with alkyl carboxylic acid (0.2 mmol), /V-hydroxyphthalimide or tetrachloro-/V-hydroxyphthalimide (0.2 mmol, 1 .0 equiv) and Lambda/,Lambda/’-dicyclohexylcarbodiimide (0.2 mmol, 1 .0 equiv). The tube was then evacuated and backfilled with argon for three times. CH2CI2 (2.0 mL) was added and the resulting mixture was stirred at room temperature for 2 h before the volatiles were removed in vacuo. MgBr2 – OEt2 (77 mg, 0.3 mmol, 1 .5 equiv) was added. The tube was evacuated and backfilled with argon for three times. Suspension A (0.8 mL, NiCI2 – 6H20 (10 mol%)/L1 (13 mol%) in THF) or suspension C (0.8 mL, NiCI2 – 6H20 (10 mol%)/L2 (13 mol%) was added. The mixture was stirred vigorously at room temperature for 15 min (or until no granular MgBr2 OEt2 was observed) and was subsequently cooled to 0 C before a suspension of [B2pin2Me]Li in THF (1 .1 mL) was added in one portion (note: do not add it dropwise). After being strred for 1 h, the reaction was warmed to room temperature and stirred for another 1 h. The reaction mixture was then quenched with 0.1 N HCI (10 mL) and extracted with Et20 (5 mLx2). The combined organic layers were dried over Na2S04, concentrated in vacuo and purified by column chromatography to give the desired product.

The chemical industry reduces the impact on the environment during synthesis 4,5,6,7-Tetrachloro-2-hydroxyisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BARAN, Phil; LI, Chao; WANG, Jie; CHATTERJEE, Arnab, Kumar; KUMAR, Manoj; YU, Shan; JOHNSON, Kristen, Ann; QIN, Tian; SHANG, Ming; (167 pag.)WO2018/175173; (2018); A1;,
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