Category: 356068-93-4

Reference of 356068-93-4, 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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 11 Preparation of 6-{5-[5-fluoro-2-oxo-1 ,2-dihydro-indol-(3Z)-ylidenemethyl]- 2,4-dimethyl-1H-pyrrole-3-carbonyl}amino-hexanoic acid methyl ester. 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyI-1H-pyrroIe-3-carbox- ylic acid (300 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethyllaminopropyI)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 6-aminocaproic acid methyl ester hydrochloride (217.8 mg, 1.2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give 6-{5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]- 2,4-dimethyl-1 H-pyrrole-3-carbonyl}amino-hexanoic acid methyl ester (346 mg, 81% yield) as a yellow solid. 1H NMR (DMSO-d6)delta1.30 (m, 2H, CH2), 1.51 (m, 2H, CH2), 1.55 (m, 2H, CH2), 2.31 (d, J= 8.0 Hz, 2H, CH2CO), 2.39 (s, 3H, pyrrole-CH3), 2.40 (s, 3H, pyrrole-CH3), 3.18 (m, 2H, NCH2), 3.57 (s, 3H, COOCH3), 6.82 (dd, J= 4.0 and 8.0 Hz, 1 H, Ar-H), 6.92 (td, J= 4.0 and 8.0 Hz, 1 H, Ar-H), 7.70 (s, 1 H, vinyl-H), 7.63 (t, J= 4.0Hz, 1 H, CONH), 7.76 (dd, J= 4.0 and 8.0 Hz, 1 H, Ar-H), 10.89 (s, 1 H, indolinone-NH), 13.66 (s, 1 H, pyrrole-NH). LC-MS (m/z) 428 (M+1).

The synthetic route of (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Application of 356068-93-4, 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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 7: Preparation of iV-(2-aminophenyl)-5-((Z)-(5-fluoro-2-oxoindolin- 3-ylidene)methyl)-2,4-dimethyl-lH-pyrrole-3-carboxamide (Compound 10)To a stirred solution of compound 109 (0.2 g, 0.67 mmol) in DMF (30 mL) at 00C was added etaOBt (0.136 g, 1.0 mmol), triethylamine (0.24 mL, 1.67 mmol), ECDI-etaC1 (0.192 g, 1.0 mmol) and benzene- 1,2-diamine (0.2 g, 2.0 mmol) successively. The mixture was stirred for 72 h at room temperature, diluted with water (20 mL), brine (20 mL) and saturated aqueous sodium bicarbonate (20 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain the product 10 as a yellow solid (0.13 g, 50.03%). LCMS: 391 [M+lf, 1H NMR (DMSO-^6): delta 4.83 (s, 2H), 6.58 (t, J= 7.2 Hz, IH), 6.78 (d, IH), 6.84 (m, IH), 6.92 (t, J= 7.8 Hz, 2H), 7.25 (d, IH), 7.74 (m,2H), 9.00 (s, IH), 10.90 (d, IH) ,13.75 (s, IH), 1H NMR (DMSO-D2O) delta 2Al (s, 3H),2.44 (s, 3H), 6.62 (t, J= 7.4 Hz, IH), 6.78 (d, IH), 6.89 ( m, IH), 6.95 (m, 2H), 7.19 (d, IH), 7.67 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 356068-93-4,Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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 stirred solution of compound 109 (220.0 mg, 0.73 mmol) in DMF (15 mL) at room temperature was added etaOBt (148.6 mg, 1.1 mmol), triethylamine(0.21 mL, 1.46 mmol), ECDI-etaC1 (210.2 mg, 1.1 mmol) and methyl 7- aminoheptanoate hydrochloride (157.1 mg, 0.8 mmol) successively. The mixture was stirred for 24 h at room temperature and was then diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL). The peta of the mixture was adjusted to 11-12 with IO N NaOH. The mixture was filtered and the solid was washed with water, dried to obtain a crude product 110-15 as a yellow solid (0.3 g, 93.2%). LCMS: 442 [M+l]+; 1H NMR(DMSO-J6): delta 1.31 (m, 4eta), 1.50 (m, 4H), 2.31 (t, J= 7.35 Hz, 2H), 2.40 ( s, 3H), 2.42 (s,3H), 3.19 (m, 2H), 3.59 (s, 3H), 6.87 (m, 2H), 7.71 (m,3H), 10.91 (s, IH), 13.67 (s, IH).

The synthetic route of 356068-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 356068-93-4, 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 356068-93-4 as follows.

To a stirred solution of compound 109 (0.2 g, 0.67 mmol) in DMF(30 mL) at O0C was added etaOBt (0.136 g, 1.0 mmol), triethylamine (0.24 mL, 1.67 mmol), ECDI etaC1 (0.192 g, 1.0 mmol) and benzene- 1,2-diamine (0.2 g, 2.0 mmol) successively. The mixture was stirred for 72 h at room temperature, diluted with water (20 mL), brine (20 mL) and saturated aqueous sodium bicarbonate (20 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain the product 10 as a yellow solid (0.13 g, 50.03%). LCMS: 391 [M+l]+, 1H NMR (DMSO-J6): delta 4.83 (s, 2eta), 6.58 (t, J= 7.2 Hz, IH), 6.78 (d, IH), 6.84 (m, IH), 6.92 (t, J= 7.8 Hz, 2H), 7.25 (d, IH), 7.74 (m,2H), 9.00 (s, IH), 10.90 (d, IH) ,13.75 (s, IH), 1H NMR (DMSO-D2O) ^ 2.41 (s, 3H),2.44 (s, 3H), 6.62 (t, J= 7.4 Hz, IH), 6.78 (d, IH), 6.89 ( m, IH), 6.95 (m, 2H), 7.19 (d, IH), 7.67 (m, 2H).

According to the analysis of related databases, 356068-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Step 5c. (Z)-Methyl 4-(2-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4- dimethyl-lH- pyrrole-3-carboxamido)ethoxy)benzoate (Compound 203)To a stirred solution of compound 109 (0.5 g, 1.67 mmol) in TetaF (150 mL) at00C was added etaOBt (0.34 g, 2.8 mmol), triethylamine (0.6 mL, 4.18 mmol),ECDI-etaC1 (0.48 g, 2.8 mmol) and compound 202 (0.6 g, 3.33 mmol) successively. The mixture was stirred overnight at room temperature, evaporated to remove solvent, diluted with water (50 mL), brine (50 mL) and saturated sodium bicarbonate solution (50 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain crude yellow solid 203 (550 mg, 69%). LCMS: 478 [M+lf, 1H NMR (DMSCM6): delta 2.40 (s, 3H), 2.43 (s, 3H), 3.63 (m, 2H),3.82 (s, 3H), 4.20 (t,2H), 6.92 (m, 2H), 7.07 (d, 2H), 7.70 (m, 2H), 7.84(s, 1H),7 .91 (d, 2H), 10.88 (s, IH), 13.68 (s, IH).

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:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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: C16H13FN2O3

Example 6 Preparation of 3-{5-[5-fluoro-2-oxo-1 ,2-dihydro-indol-(3Z)-ylidenemethyl]- 2,4-dimethyl-1 H-pyrrole-3-carbonyl}amino-propionic acid methyl ester. 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbox- ylic acid (300 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and beta-alanine methyl ester hydrochloride (168.6 mg, 1.2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give 2-{5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-car- bonyljamino-propionic acid methyl ester (333 mg, 87% yield) as a yellow solid. 1H NMR (DMSO-d6)delta2.39 (s, 3H, pyrrole-CH3), 2.41 (s, 3H, pyrrole-CH3), 2.58 (d, J= 8.0 Hz, 2H, CH2CO), 3.50 (m, 2H, NCH2), 3.63 (s, 3H, COOCH3), 6.84 (dd, J= 4.0 and 8.0 Hz, 1H, Ar-H), 6.92 (td, J= 4.0 and 8.0 Hz, 1H, Ar-H), 7.70 (s, 1H, vinyl-H), 7.67 (t, J= 4.0Hz, 1H, CONH), 7.75 (dd, J= 4.0 and 8.0 Hz, 1H1 Ar-H), 10.88 (s, 1 H, indolinone-NH), 13.66 (s, 1H, pyrrole-NH). LC-MS (m/z) 386 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 356068-93-4, its application will become more common.

Reference:
Patent; SHENZEN CHIPSCREEN BIOSCIENCE, LTD.; WO2009/14941; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 356068-93-4,Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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 9: Preparation of (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)- TV- (7-(hydroxyl-amino)-7-oxoheptyl)-2,4-dimethyl-lH-pyrrole- 3-carboxamide (Compound 15) Step 9a. (Z)-Methyl 7-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl- lH-pyrrole-3-carboxamido)heptanoate (Compound 110-15)To a stirred solution of compound 109 (220.0 mg, 0.73 mmol) in DMF (15 mL) at room temperature was added etaOBt (148.6 mg, 1.1 mmol), triethylamine(0.21 mL, 1.46 mmol), ECDI-etaC1 (210.2 mg, 1.1 mmol) and methyl 7- aminoheptanoate hydrochloride (157.1 mg, 0.8 mmol) successively. The mixture was stirred for 24 h at room temperature and was then diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL). The peta of the mixture was adjusted to 11-12 with 10 N NaOH. The mixture was filtered and the solid was washed with water, dried to obtain a crude product 110-15 as a yellow solid (0.3 g, 93.2%). LCMS: 442 [M+lf; 1H NMR(DMSO-^6): delta 1.31 (m, 4H), 1.50 (m, 4H), 2.31 (t, J= 7.35 Hz, 2H), 2.40 ( s, 3H), 2.42 (s,3H), 3.19 (m, 2H), 3.59 (s, 3H), 6.87 (m, 2H), 7.71 (m,3H), 10.91 (s, IH), 13.67 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 356068-93-4,Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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.

Step 8d. (?)-Methyl 3-(4-(2-(5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4- dimethyl -lH-pyrrole-3-carboxamido)ethoxy)phenyl)acrylate (Compound 304) To a stirred solution of compound 109 (0.5 g, 1.67 mmol) in DMF( 40 mL) at00C was added etaOBt (0.34 g, 2.5 mmol), triethylamine (0.94 mL, 6.68 mmol), ECDI-HCl (0.48 g, 2.5 mmol) and compound 303 (0.44 g, 2.0 mmol) successively. The mixture was stirred overnight at room temperature, evaporated, diluted with water (50 mL), brine (50 mL) and saturated aqueous sodium bicarbonate(50 mL). The pH of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain desired product 304 as a yellow solid (630 mg, 75%). LCMS: 504 [M+l]+, 1H NMR (DMSO-^6): delta 2.39 (s, 3H), 2.41 (s, 3H), 3.59 (m, 2H), 3.69 (s, 3H), 4.15 (t, J= 4.5 Hz, 2H), 6.45 (d, IH), 6.94 (m, 4H), 7.65 (m, 6H), 10.87 (s, IH), 13.66 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem