Indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, 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 100510-65-4, name: 6-Amino-3,3-dimethylindolin-2-one

Example No.11: 6-(4-(Cyclopropylamino)furo[3,2-i/|pyrimidin-2-ylamino)-3,3- dimethylindolin-2-oneTo a flask was added 2-chloro-A^-cyclopropylfuro[3,2-i/]pyrimidin-4-amine (0.45 g, 2.14 mmol, Example No.3, Step C), 6-amino-3,3-dimethylindolin-2-one (0.378 g, 2.14 mmol, Astatech), K2C03 (0.89 g, 6.44 mmol) and i-AmOH (5 mL). To the mixture was added Pd2dba3 (0.1 18 g, 0.129 mmol) and X-Phos (0.123 g, 0.258 mmol). The mixture was heated to about 100 C and stirred for about 15 h. The mixture was filtered and the filtrate was directly purified by column chromatography eluting with 0 to 70% of 10% MeOH/DCM (containing 2M 1.5% NH3 in EtOH) and DCM (25 g silica gel)). The material was then dried in a vacuum oven at about 65 C for about 48 h. The solid was then suspended in Et20 (5 mL), sonicated for 2 min and filtered. The solid was dried in a vacuum oven at about 80 C for about 16 h to give 6-(4- (cyclopropylamino)furo[3,2-ii|pyrimidin-2-ylamino)-3,3-dimethylindolin-2-one (0.195 g, 26%o): LC/MS (Table 2, Method c) R, = 1.81 min.; MS m/z: 350 (M+H)+. Syk IC50 = A

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, 6-Amino-3,3-dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
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Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

General procedure: Compound 7 (2.1 g, 0.012 mol) and HBTU (5.0 g, 0.013 mol) were dissolved in dry DMF, in a 250 ml round bottom flask. DIPEA (6.5 ml, 0.037 mol) was added and the reaction mixtures were stirred for 30 min. L or D- phenylalanine methyl ester hydrochloride (3.0 g, 0.014 mol) or glutamic acid dimethyl ester hydrochloride (3.0 g 0.014 mol) was added and the reaction mixture was kept stirring overnight under ambient conditions. Reaction monitoring by TLC was performed on silica gel plates using CHCl3:MeOH 9:1 as eluent. Saturated NaHCO3 solution (150 ml) was added to the mixture and the precipitate was filtered, washed with saturated NaHCO3 solution and water. The crude product was purified by column chromatography CHCl3:MeOH (95:5) to give the product as white to off-white solid.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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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. 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C26H31N3O8

General procedure: 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H-indol-1-yl}Propyl benzoate(2R, 3R) -mono-tartaric acid salt(Mono-tartaric acid salt of the compound of formula (II)),Potassium carbonate (80 g),And a mixed solvent of acetonitrile and dimethylacetamide (ACN / DMAC = 500 mL / 500 mL) was heated to 80 DEG C,Stir for 30 min. To the reaction mixture were added 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula 3) and 9.70 g of KI,The reaction was carried out at the same temperature for 10 hours.The reaction mixture was cooled to room temperature,And extracted with 1 L of ethyl acetate and 1.5 L of water.The organic layer obtained by layer separation was washed with 1 L of brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing again with 200 mL of ethyl acetate, the solvent was removed by distillation. 400 mL of methanol, 100 mL of water and 20 g of KOH were added to the obtained residue. After the mixture was stirred at room temperature for 10 hours,1 L of ethyl acetate and 1 L of water were added and extracted for 10 minutes.The organic layer obtained by layer separation was washed sequentially with 1 L of saturated aqueous solution and 1 L of saturated brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing with 200 mL of ethyl acetate,18 g of oxalic acid was added.The reaction mixture was stirred at 50 for 30 minutes, It cooled to room temperature.600 mL of isopropyl ether was added to the reaction mixture,Stirred for 2 hours, and then filtered.The obtained crystals were washed with 200 mL of isopropyl ether,At 40 for 10 hours to give the titled compound as a dried in vacuo to 88 g.The reaction was carried out in the same manner as in Example 1, except that 23 g of succinic acid was used instead of oxalic acid to obtain 92 g of tabular compound.Yield: 82%Purity: 99.5%Impurities (dimer): Not more than 0.1%

The synthetic route of 239463-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dasan Medichem Co., Ltd.; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Kim, Jae Hyung; Aum, Woon Yong; (12 pag.)KR2016/92976; (2016); A;,
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Synthetic Route of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: 4.4.18 (Z)-5-methoxy-3-((2-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazol-6-yl)methylene)indolin-2-one (5r) Compound 5r was prepared according to the method described for compound 5a, employing aldehyde 11e (156 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81 mg, 0.5 mmol) to obtain the pure product 5r as a yellow solid (134 mg, 59%); mp: 168-166 C; IR (KBr): 3425, 3174, 2354, 1690, 1640, 1575, 1488, 1435, 1280, 1120, 1032, 992, 846, 742 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.34 (bs, 1H), 7.89 (s, 1H), 7.77 (s, 1H), 7.66 (d, J = 8.1 Hz, 1H), 7.58 (s, 1H), 7.54 (s, 2H), 7.36 (s, 1H), 6.89-6.66 (m, 2H), 3.92 (s, 6H), 3.76 (s, 3H), 3.62 (s, 3H); 13C NMR (75 MHz, CDCl3 + DMSO-d6): delta 168.9, 153.7, 153.0, 139.0, 137.3, 136.3, 128.2, 127.7, 126.2, 124.8, 121.9, 114.2, 113.8, 111.2, 111.1, 110.0, 108.9, 108.5, 103.8, 59.9, 55.8, 55.0; MS (ESI): m/z 458 [M + H]+; HRMS (ESI) calcd for C26H24O5N3 m/z 458.16992 [M + H]+; found 458.17105.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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Synthetic Route of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0¡ãC. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0¡ãC for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10percent acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80percent). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J? 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

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

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
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24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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. Formula: C14H16BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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. Recommanded Product: 19155-24-9

Step 4:3,3-dimethyl-2,3-dihydro-1H-indoleUnder a nitrogen atmosphere a solution of 6.20 mL (6.20 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.00 g (6.20 mmol) 3,3-dimethyl-1,3-dihydro-indol-2-one in 50 mL THF.Then the reaction mixture was heated to 60¡ã C. for 1 h.After cooling to 0¡ã C., 3 mL ice water were slowly added dropwise.20 g sodium sulphate were added and the mixture was suction filtered.The solution was evaporated down i. vac.Yield: 0.80 g (88percent of theory)ESI-MS: m/z=148 (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 19155-24-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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Electric Literature of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 3 was prepared by the condensation of commercially available aminoacetaldehyde diethyl acetal with the phthalic anhydride (1:1 mol ratio), using toluene under reflux, in the presence of a catalytic amount of DMAP (yield 52percent) for 2 h. In the next step, 2-(2,2-diethoxyethyl)isoindoline-1,3-dione (3) underwent acid hydrolysis (sulphuric acid at 70percent) in reflux for 2 h. After the reaction was completed, it was allowed to reach at room temperature and was then cooled to induce precipitation. The formed precipitate was filtered on a sintered funnel with distilled water, yielding 55percent of the pure product. For the synthesis of 5a and 5b, 2-(1,3-dioxoisoindol-2-yl) acetaldehyde (4) reacted with thiosemicarbazide (in the ratio 1:1) (for 5a) or 4-phenyl-3-thiosemicarbazide (for 5b), in ethanol, under reflux with catalytic amount of HCl (4 drops) for 4 h. The reactions were followed by thin layer chromatographic plate analysis. The formed precipitate was filtered on a sintered funnel with ethanol to yield the pure product (yield 76percent for 5a and 70percent for 5b). 4.1.3.1 (E)-2-[2-(1,3-dioxoisoindolin-2-yl)ethylidene]hydrazinecarbothioamide (5a) White crystals; Yield: 76percent; m.p. (¡ãC) 223-224; Rf 0.45 (hexane/ethyl acetate 3:2); IR (KBr, cm-1): 3423 and 3308 (N-H), 1769 and 1713 (C=O), 1602 (C=N); 1H NMR (300 MHz, DMSO-d6), delta ppm: 4.36 (d, J = 3.6 Hz, 2H, CH2), 7.36 (s, 1H, NH), 7.42 (t, J = 3.6 Hz, 1H, CH=N), 7.83-7.90 (m, 4H, Ar), 8.03 and 11.27 (s, 1H, NH2); 13C NMR (75.5 MHz, DMSO-d6), delta ppm: 40.1 (CH2), 123.1 (Ar), 131.7 (Ar), 134.4 (Ar), 140.4 (C=N), 167.5 (C=O), 177.9 (C=S). Anal. Calcd for C11H10N4O2S: C, 50.37; H, 3.84; N, 21.36; S, 12.22. found: C, 50.03; H, 3.45; N, 20.98; S, 12.30. HRMS: 262.3388 [M+H] +.

The chemical industry reduces the impact on the environment during synthesis N-(2-Oxoethyl)phthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Article; De Moraes Gomes, Paulo Andre Teixeira; Oliveira, Arsenio Rodrigues; De Oliveira Cardoso, Marcos Verissimo; De Farias Santiago, Edna; De Oliveira Barbosa, Miria; De Siqueira, Lucianna Rabelo Pessoa; Moreira, Diogo Rodrigo Magalhaes; Bastos, Tanira Matutino; Brayner, Fabio Andre; Soares, Milena Botelho Pereira; De Oliveira Mendes, Andresa Pereira; De Castro, Maria Carolina Accioly Brelaz; Pereira, Valeria Rego Alves; Leite, Ana Cristina Lima; European Journal of Medicinal Chemistry; vol. 111; (2016); p. 46 – 57;,
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Electric Literature of 3891-07-4, These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)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.

Preparation of Ethyl 4-[2-(PHTHALIMIDO) ETHOXY] ACEFOACETATE (X1 A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 75 mL of tetrahydrofuran under nitrogen atmosphere. 7.53 g Sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 20 g of N- (2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 16.35 g ethyl 4-chloroacetoacetate in 30 ML of TETRAHYDRAFURAN was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 10 mL ethanol. The mixture was then poured into 150 mL of IN hydrochloric acid solution in crushed ice and 200 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of 5 wt. % OF NAHC03 solution, then with 150 ML of water, dried over 5 G of MgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 15 mL of hexane to remove the mineral oil to give 17.2 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate light brown product. (yield 51%, rel. compound purity > 80%). IR (KBR, CM~L) : 2995 and 1716. 1H-NMR (CDC13) 6 7.76 (dd, 2H), 7.65 (dd, 2H), 4.11 (S, 2H), 4.02 (q, 2H), 3.80 (t, 2H), 3.70 (t, 2H), 3.37 (s, 2H), 1. 16 (t, 3H). 13C-NMR (CDC13) 8 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 61.6, 46.0, 37.4, 14.3.

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
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Electric Literature of 3676-85-5, 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 3676-85-5 as follows.

Inthe above reaction scheme, the compound6and 7 was synthesized by literature procedure[2]. To a boiling ethanol solution (10 mL) of 7 (0.2 mmol, 30 mg) was added hydrazinehydrate 50% (0.2 mmol, 1 mL). Thereaction mixture was refluxed at 80 oC for 45 min. After completionof the reaction the reaction mixture was cooled in ice water bath, theprecipitate was collected and dried in room temperature. (Color: yellow solid;Yield: 25 mg (74%)). 1H-NMR spectrum of 8(DMSO-d6, 300MHz, ppm): delta 5.73 (s, 2H), 6.53 (s, 1H), 6.56 (s,1H), 7.30 (d, J = 8.4 Hz, 2H), 7.80 (s, 1H); 13C-NMRspectrum of 8 (DMSO-d6, 75MHz, ppm): delta 157.6, 154.3, 152.9, 128.8, 117.2, 119.3, 116.5, 106.0. 1 H-NMR spectrum of 7 (DMSO-d6,300 MHz, ppm): delta 5.54, (s 2H), 6.83 (dd, J = 6.1 Hz, 1H), 6.9 (d, J = 2.1 Hz, 1H), 7.48 (d, J = 8.4Hz, 1H), 7.58 (s, 1H), 10.24 (s, 1H).FTIR spectrum of 6, 7and8, FTIR (ATR)(nu,cm-1): 3317 (N-H), 1695 (C=O), 1543,1340 (N-O), 1070, 1301 (C-O), 715 (C-H); 3440 (N-H), 1710 (C=O), 1381, 1072 (C-O),746 (C-H) and 3740 (N-H), 1640 (C=O), 1407, 1072 (C-O), 719 (C-H),respectively. UV-Visible absorption of8(c 0.564¡Á10-4 mol/ L, C2H5OH); UV (C2H5OH)lambdamax(log epsilon) 273 (1.949).

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Daniel Thangadurai; Nithya; Rakkiyanasamy; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 211; (2019); p. 132 – 140;,
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