Category: 132898-96-5

Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, Recommanded Product: 132898-96-5

To a mixture of 2,3-dioxoindoline-5-sulfonyl chloride (0.800 g, 3.26 mmol) in dry THF (10 ml), cooled at 0 C. under nitrogen, DIPEA (1.138 ml, 6.51 mmol) and dimethylamine 2M in THF (2.117 ml, 4.23 mmol) were added, and the mixture was allowed to stir at room temperature for 2.5 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give N,N-dimethyl-2,3-dioxoindoline-5-sulfonamide (0.639 g, 2.51 mmol, 77% yield). MS/ESI+ 254.9 [MH]+.

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Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5, A common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

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; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 132898-96-5, The chemical industry reduces the impact on the environment during synthesis 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

Step 3: 3,3-Dimethyl-8-{[(2S)-2-(phenoxymethyl)-2,3-dihydro-1H-indol-1-yl]sulfonyl }-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one The title compound was prepared from 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride and (S)-2-phenoxymethyl-2,3-dihydro-1H-indole as a yellow foam according to a procedure similar to that of Example 12. NMR (400 Mz, DMSO-d6): consistent. MS: (ES-) m/z 500 [M-H].

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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 132898-96-5, These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

The synthetic route of 132898-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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 cis-N-benzyl-2,5-bis(methoxymethyl)pyrrolidine (18a) (620 mg, 2.49 mmol, 1.00 equiv.) and 10% Pd/C (62 mg, 10% w/w) in MeOH (12 mL) was stirred in an autoclave at ambient temperature under H2 atmosphere (20 atm) for 6 h. After this time, the mixture was filtered through Celite and washed again with MeOH. The solvent was removed under reduced pressure to obtain the corresponding unprotected bis(methoxymethyl)pyrrolidine as a light yellow oil. The solution of obtained free amine cis-2,5-bis(methoxymethyl)pyrrolidine and DIPEA (766 muL, 4.40 mmol, 2.00 equiv.) in CHCl3 (5 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.08 g, 4.40 mmol, 2.00 equiv.) in CHCl3/THF (1:1, 50 mL) at room temperature. The resulting mixture was stirred further for 2 h and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 90% EtOAc in cyclohexane) to yield a yellow solid (723 mg, 1.96 mmol, 89%). M.p. 168 C. 1H NMR (400 MHz, DMSO-d6): delta = 11.46 (br s, 1H, 1-NH), 8.05 (dd, 3JH,H = 8.3 Hz, 4JH,H = 2.0 Hz, 1H, 6-CH), 7.80 (d, 4JH,H = 1.9 Hz, 1H, 4-CH), 7.09 (d, 3JH,H = 8.3 Hz, 1H, 7-CH), 3.73-3.58 (m, 2H, 12-CH, 15-CH), 3.52-3.20 (m, 4H, 16-CH2, 19-CH2), 3.37 (s, 6H, 18-CH3, 21-CH3), 1.78-1.62 (m, 2H, 13-CHa, 14-CHa), 1.57-1.37 (m, 2H, 13-CHb, 14-CHb) ppm. 13C NMR (100 MHz, DMSO-d6): delta = 182.9 (3-CO), 159.4 (2-CO), 153.6 (8-CN), 136.7 (6-CH), 130.8 (5-CSO2), 123.1 (4-CH), 118.1 (9-CCO), 112.7 (7-CH), 74.4 (2C, 16-CH2, 19-CH2), 59.9 (2C, 12-CH, 15-CH), 58.4 (2C, 18-CH3, 21-CH3), 26.9 (2C, 13-CH2, 14-CH2) ppm. HRMS (ESI+, MeOH): m/z = 391.0931 [M + Na]+, 423.1194 [M + Na + MeOH]+; calcd. 391.0934 for C16H20N2O6S + Na, 423.1196 for C16H20N2O6S + Na + MeOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dioxoindoline-5-sulfonyl chloride, its application will become more common.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

The synthetic route of 2,3-Dioxoindoline-5-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, category: indolines-derivatives

Step 1: 5-{[(2S)-2-(Phenoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold solution of 2,3-dioxo-2,3-dihydro-1-H-indole-5-sulfonylchloride (3.80 g, 15.5 mmol) in a 1:1 mixture of THF:CHCl3 (194 mL) was added drop-wise via syringe pump a solution of (2S)-2-(phenoxymethyl)pyrrolidine (2.85 g, 16.1 mmol, 1.03 eq) (J. Med. Chem, 44, 2014, 2001) and N,N-diisopropylethylamine (5.61 mL, 32.2 mmol, 2 eq) in CHCl3 (30 mL) over a period of 50 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring at room temperature for 64 hr the reaction mixture was concentrated and the crude product was flash chromatographed twice using Biotage KP silica gel, and gradient of 98/2 CH2Cl2/CH3OH as eluent on the first column and 90/10 CH2Cl2/CH3OH as eluent on the second column to give the title compound as a dark green solid (5.29 g, 88% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (ES-) m/z 385 [M-H]. MS: (ES+) m/z 387 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dioxoindoline-5-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, name: 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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. Safety of 2,3-Dioxoindoline-5-sulfonyl chloride

A solution of rpml21 (0.211 g, 0.861 mmol) and morpholine (0.187 g, 2.139 mmol, 2.5 eq), in anhydrous DCM (7 ml) and anhydrous chloroform (1 ml) was stirred for 3h at room temperature under Ar. The yellow precipitate was collected by filtration and dried under vacuum. The crude product 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 132898-96-5, its application will become more common.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; WO2007/117699; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem