Category: indolines-derivatives

Related Products of 132898-96-5, 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 132898-96-5 as follows.

Example 4 (S)-5-(2-Phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (10). To a solution of 9 (1.46 g, 5.2 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) at 0 C. The mixture was stirred at 0 C. for 15 min. After evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL) were added, then a solution of 6 (1.44 g, 5.9 mmol) in THF (25 mL) was added at 0 C. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, then ethyl acetate (150 mL) was added, washed with water (50 mL*2) and saturated NaCl (50 mL), and dried over Na2SO4. After evaporation of the ethyl acetate, the crude product was purified with ether to afford 1.7 g (84%) of 10 as a yellow solid, mp 204.5-205.9 C. 1H NMR (300 MHz, CDCl3) delta 8.94 (s, 1H), 7.77 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.84 (d, J=8.1 Hz, 1H), 6.69 (t, J=7.2 Hz, 1H), 6.63 (d, J=7.8 Hz, 2H), 3.89 (m, 1H), 3.75-3.66 (m, 2H), 3.23 (m, 1H), 2.96 (m, 1H), 1.72 (m, 2H), 1.54-1.42 (m, 2H). LRMS (FAB) m/e: 387.1 (M+H, 100). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70; N, 7.25. Found: C, 58.99, H, 4.74, N, 7.11.

According to the analysis of related databases, 132898-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Washington University in St. Louis; US2009/68105; (2009); A1;,
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Related Products of 2058-72-2, 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 2058-72-2 as follows.

General procedure: Dialkyl acetylenedicarboxylate 2 (1 mmol) was added to a magnetically stirred 5 mL flat bottom flask containing hydrazine hydrate (1 mmol) and H2O (2 mL) at room temperature. After 10 min, isatin 1(1 mmol) malononitrile (1 mmol) and NaCl (20 mol %) were added and the reaction heated at 50 C for 10 min. After completion of the reaction (monitoring by TLC), the reaction mixture was filtered and the precipitate washed with water and then ether to afford the pure products 3a-h. Methyl 6?-amino-5-bromo-5?-cyano-1-methyl-2-oxo-1?H-spiro-[indoline-3,4?-pyrano[2,3-c]pyrazole]-3?-carboxylate (3g): Yellow powder; yield: 0.25 (80%); m.p. 275-276 C; IR (KBr): 3432, 3307, 3173 (NH2and 2NH), 2200 (C?N), 1720 (CO2Me), 1698 (NCO), 1638, 1602, 1487 (Ar), 1190 (C-O) cm-1; 1H NMR: delta3.35 (3H, s, NCH3), 3.48 (3H, s, OCH3), 7.09 (1H, d, 3JHH= 7.6 Hz, CH6of Ar), 7.31 (1H, s, CH4of Ar), 7.44 (2H, s, NH2), 7.50 (1H, d, 3JHH= 7.2 Hz, CH7of Ar), 14.05 (1H, s, NH) ; 13C NMR: delta26.5 (NCH3), 47.0 (Cspiro), 52.0 (OCH3), 55.5 (C-CN), 99.8 (C3?), 110.2 (CH7), 114.3 (C-Br), 117.8 (CN), 126.4 (CH4), 128.3 (C3a), 131.3 (CH6), 135.2 (C-CO2Me), 142.9 (C7a), 155.9 (OCN), 157.6 (CO2Me), 161.2 (C-NH2), 175.4 (C=O of isatin); MS (EI, 70 eV): m/z (%) = 430 [M+], 403, 287, 142, 101, 83, 59. Anal. calcd for C17H12BrN5O4(430.21): C, 47.46; H, 2.81; N, 16.28; found: C, 47.39; H, 2.74; N, 16.37%.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alizadeh, Abdolali; Moafi, Leila; Journal of Chemical Research; vol. 39; 8; (2015); p. 464 – 466;,
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Related Products of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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.

General procedure: A mixture of compound [3-7]a-i (0.01mole) and thionyl chloride (0.01mole) placed in dry benzene (10 ml.) and refluxed for 7 hours. The excess of thionyl chloride and benzene were removed under vacuum after cooling .

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Samir, Ali H.; Saeed, Ruwaidah S.; Matty, Fadhel S.; Oriental Journal of Chemistry; vol. 34; 1; (2018); p. 286 – 294;,
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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 446292-08-6 as follows. Computed Properties of C22H19N3O6

100 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione of Formula (I), 1000 ml Methanol and 119 g methyl amine were added to RBF at 25 C. to 35 C. The reaction was heated to 60 C. to 65 C. for 1-2 hours. To the reaction mass formic acid (15 g) was added till to pH 5.5 to 6.0 and maintained for 30 minutes. The reaction mass was cooled to 45 to 50 C. and maintained for 30 minutes. The reaction mass was cooled to 25 to 35 C. and maintained for 30 minutes. The product was filtered and washed with methanol (50 ml*2) afforded the formate salt of (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one of Formula (JF).

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); A1;,
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Application of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromoisoindolin-1-one (636 mg,3.0 mmol), 1D (800 mg, 3.0 mmol), Pd2(dba)3 (82 mg, 0.09 mmol), Xantphos (52 mg, 0.09 mmol) and Cs2CO3 (1.17 g, 3.6 mmol) in dioxane (60 mE) was heated to 1000 C. for 4 h. After that time, the mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel (1%-10% EtOAc in pet. ether) to afford 5A (400 mg, 34%) as a yellow solid: ?H NMR (400 MHz, DMSO-d5) oe8.71 (s, 1H), 8.61 (d, J=8.4 Hz, 1H), 8.07 (t, J=8.4 Hz, 1H),8.0 (d, J=7.6 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 7.76 (d, J=3.2 Hz, 2H), 5.17 (s, 2H), 4.11-4.04 (m, 1H), 1.14-1.11 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 396.1, 398.1 [M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); 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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 19727-83-4

To an oven dried flask equipped with a stir bar cooled under argon was added 6-nitroindoline (2.0 grams, 12.2 mmol) and 61.0 mL of anhydrous drichloromethane. While stirring at 0 C 2- methoxyacetyl chloride (1.3 mL, 14.6 mmol) was added followed by triethylamine (2.2 mL, 16 mmol). The reaction slowly warmed to room temperature. Once complete, determined by LCMS, the reaction was quenched with water, and the organic material extracted using dichloromethane. The aqueous material was washed with dichloromethane twice. The combined organic material was washed with NaHC03 (sat.), brine, dried with Na2S04, filtered and concentrated. The crude material was then used without further purification.

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 19727-83-4.

Reference:
Patent; MUSC FOUNDATION FOR RESEARCH DEVELOPMENT; U.S. DEPARTMENT OF VETERANS AFFAIRS; LINDSEY, Christopher, C.; BEESON, Craig, C.; SCHNELLMANN, Rick, G.; (51 pag.)WO2018/85491; (2018); A1;,
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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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6ClNO2

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. .1.54 2-((2-(2-(Butan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (2C) White powder, mp 135-142 C, 87% yield; 1H NMR (400 MHz, CDCl3): delta 1.08-1.12 (t, 3H, CH3), 2.20 (s, 3H, CH3), 2.27-2.31 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.76 (bs, 2H, Ar), 7.86-7.87 (m, 2H, Ar).

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; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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Application of 5181-35-1,Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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 2-(2-bromoetho xy)isoindo line- 1,3- dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 10) and 2H-tetrazole-5-carboxylic acid ethyl ester (10.51 g, 74 mmol) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at room temperature. After 16 hours, the reaction mixture was filtered through filter paper and filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes of stirring, the product was extracted with ethyl acetate (200 ml and 100 ml). The combined organic layers were washed with brine (100 ml). The organic extract was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 12.5 g of the titled compound. The compound was purified by column chromatography using mixture of acetone and hexane as an eluent. The fractions containing the compound were collected and concentrated to provide 10 g of mixture of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}-2H-tetrazole-5-carboxylate in 53% yield Analysis: Mass: 332(M+1); for Molecular weight: 331 and for Molecular formula: C14H13N5O5 ; To a solution of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}-2H-tetrazole-5-carboxylate (10 g, 3.02 mmol, product from step 1) in dichloromethane (100 ml) was added hydrazine hydrate (2.26 ml, 4.53 mmol) at 25- 30 C under stirring. The stirring was continued for 2 hours and the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent. After complete conversion of starting material, the unwanted solid was filtered out and washed with dichloromethane (20 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 6.0 g of mixture of ethyl l-[2-(aminooxy)ethyl]- lH-tetrazole-5-carboxylate and ethyl 2- [2-(aminooxy)ethyl]-2H-tetrazole-5-carboxylate (about 100% yield), the resulted compound was used in the next step without further purification.

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

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Indoline | C8H9N – PubChem

Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

Example 46 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)- phenyl)-2-(2-(5-(methylsulfonamidomethyl)-1 ,3-dioxoisoindolin-2- yl)acetoxy)ethyl)pyridine 1 -oxide (Compound 254): Scheme 46 Step 1 : Preparation of 1 ,3-dioxoisoindoline-5-carbonitrile (249): A mixture of 5-bromoisoindoline-1 ,3-dione (2.5 g, 1 1 .06 mmol) and Pd(Ph3P)4 (1 .406 g, 1 .217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1 .299 g, 1 1 .06 mmol) was added and the solution, splitted in 5 vials, was heated under microwave irradiation at 200C for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added and the organic phase was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM: MeOH = 99: 1 ) to afford 1 ,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH] +).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; CARZANIGA, Laura; LA PORTA, Elena; GUALA, Matilde; WO2013/57013; (2013); A2;,
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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 39603-24-2 as follows. Formula: C10H9NO2

General procedure: A solution of isatin (1 mmol), barbituric acid (1 mmol), 3-amino-5-methyl isoxazole (1 mmol), and p-TsOH (0.2 mmol) in water (10 mL) was stirred for 24 h at 70 C in oil bath. After completion of the reaction, which was followed by TLC (n-hexane/EtOAc), the warm reaction mixture was filtered. The residue was washed with water and then recrystallized from ethanol to give the pure product.

According to the analysis of related databases, 39603-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rahmati, Abbas; Khalesi, Zahra; Tetrahedron; vol. 68; 40; (2012); p. 8472 – 8479;,
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