Category: 21905-86-2

Cinnoline-4-carboxylic acid, A common heterocyclic compound, 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.”21905-86-2

10764] To a stirred solution of N1-cyclopropyl-5-fluo- robenzene-1,2-diamine mt-i (500 mg, 3.01 mmol) in DMF (5 mE) under an inert atmosphere was added cinnoline-4- carboxylic acid (524 mg, 3.01 mmol), HATU (1.71 g, 4.51 mmol) and diisopropylethylamine (1 mE, 6.02 mmol) at 00 C. The reaction mixture was stirred at room temperature for 16 h. Afier consumption of starting material (by TEC), the reaction mixture was diluted with water (20 mE) and extracted with EtOAc (2×20 mE). The combined organic extracts were washed with water (20 mE), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain N-(2-(cyclopropylamino)-4-fluorophenyl) cinnoline4-carboxamide (500 mg, crude) as brown solid used in the next step without further purification.10765] EC-MS: m/z 322.9 [M+H] at 2.71 RT (38.30% purity).

The chemical industry reduces the impact on the environment during synthesis, Cinnoline-4-carboxylic acid, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; Hoekstra, William J.; (156 pag.)US2018/185362; (2018); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

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.21905-86-2, Cinnoline-4-carboxylic acid it is a common compound, a new synthetic route is introduced below.21905-86-2

EXAMPLE 5 n-Propyl Cinnoline-4-carboxylate (5) A suspension of 870 mg of 1, and 850 mg of carbonyidimidazole (CDII) in 30 ml of tetrahydrofuran (THF) was stirred at room temperature until CO2 evolution ceased (ca. 30 minutes). After being stirred for 2 hours, the resulting mixture was treated with 320 mg of dry nypropanol and 3 drops of a 0.1 M solution of sodium imidazole in THE. The mixture was held at room temperature overnight, then the solvent was evaporated and the residue was partitioned between water and ether. The etheral extract was washed with saturated sodium bicarbonate solution, then with brine, then dried (MgSO4) and stripped in a rotary evaporator. The residue was chromatographed over silica gel, using a 1:1 v:v mixture of cyclohexane and ethyl acetate as eluent, to give 5, as a yellow oil.

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 Cinnoline-4-carboxylic acid reaction routes.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Cinnoline-4-carboxylic acid, A common heterocyclic compound, 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.”21905-86-2

10764] To a stirred solution of N1-cyclopropyl-5-fluo- robenzene-1,2-diamine mt-i (500 mg, 3.01 mmol) in DMF (5 mE) under an inert atmosphere was added cinnoline-4- carboxylic acid (524 mg, 3.01 mmol), HATU (1.71 g, 4.51 mmol) and diisopropylethylamine (1 mE, 6.02 mmol) at 00 C. The reaction mixture was stirred at room temperature for 16 h. Afier consumption of starting material (by TEC), the reaction mixture was diluted with water (20 mE) and extracted with EtOAc (2×20 mE). The combined organic extracts were washed with water (20 mE), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain N-(2-(cyclopropylamino)-4-fluorophenyl) cinnoline4-carboxamide (500 mg, crude) as brown solid used in the next step without further purification.10765] EC-MS: m/z 322.9 [M+H] at 2.71 RT (38.30% purity).

The chemical industry reduces the impact on the environment during synthesis, Cinnoline-4-carboxylic acid, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; Hoekstra, William J.; (156 pag.)US2018/185362; (2018); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2, A common heterocyclic compound, 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.”21905-86-2

1-(Ethoxycarbonyl)ethyl Cinnoline-4-carboxylate (32) A solution of 0.75 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 20 ml of benzene was added to a stirred suspension of 0.87 g of 1 in 30 ml of benzene at room temperature. After one hour of stirring, 1.36 g of ethyl 2-bromopropionate was added and the mixture was heated at reflux for 6 hours. The mixture was cooled, diluted with 25 ml of benzene, washed with water, 1 N aqueous sodium bicarbonate, and brine. It then was dried (MgSO4), the solvent was evaporated and the residue was chromatographed on silica gel, using a 1:1 v:v mixture of cyclohexane and ethyl acetate as eluent, to give 32, as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2, A common heterocyclic compound, 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.”21905-86-2

EXAMPLE 2 Potassium Cinnoline-4-carboxylate (2) 5.10 g of (1) was added over 30 minutes to a vigorously stirred solution of 2.02 g of potassium carbonate in 25 ml of water, at room temperature. The resulting mixture was stirred for one hour at room temperature, then treated with charcoal, and after filtration the water was evaporated. The residue was azeotropically distilled with toluene and dried at 70 C. under reduced pressure, to give 2, as a light tan powder, m.p.: above 280 C., 21905-86-2

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

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.21905-86-2, Cinnoline-4-carboxylic acid it is a common compound, a new synthetic route is introduced below.21905-86-2

EXAMPLE 2 Potassium Cinnoline-4-carboxylate (2) 5.10 g of (1) was added over 30 minutes to a vigorously stirred solution of 2.02 g of potassium carbonate in 25 ml of water, at room temperature. The resulting mixture was stirred for one hour at room temperature, then treated with charcoal, and after filtration the water was evaporated. The residue was azeotropically distilled with toluene and dried at 70 C. under reduced pressure, to give 2, as a light tan powder, m.p.: above 280 C.

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 Cinnoline-4-carboxylic acid reaction routes.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2, A common heterocyclic compound, 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.”21905-86-2

10764] To a stirred solution of N1-cyclopropyl-5-fluo- robenzene-1,2-diamine mt-i (500 mg, 3.01 mmol) in DMF (5 mE) under an inert atmosphere was added cinnoline-4- carboxylic acid (524 mg, 3.01 mmol), HATU (1.71 g, 4.51 mmol) and diisopropylethylamine (1 mE, 6.02 mmol) at 00 C. The reaction mixture was stirred at room temperature for 16 h. Afier consumption of starting material (by TEC), the reaction mixture was diluted with water (20 mE) and extracted with EtOAc (2×20 mE). The combined organic extracts were washed with water (20 mE), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain N-(2-(cyclopropylamino)-4-fluorophenyl) cinnoline4-carboxamide (500 mg, crude) as brown solid used in the next step without further purification.10765] EC-MS: m/z 322.9 [M+H] at 2.71 RT (38.30% purity).

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; Hoekstra, William J.; (156 pag.)US2018/185362; (2018); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2, A common heterocyclic compound, 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.”21905-86-2

EXAMPLE 2 Potassium Cinnoline-4-carboxylate (2) 5.10 g of (1) was added over 30 minutes to a vigorously stirred solution of 2.02 g of potassium carbonate in 25 ml of water, at room temperature. The resulting mixture was stirred for one hour at room temperature, then treated with charcoal, and after filtration the water was evaporated. The residue was azeotropically distilled with toluene and dried at 70 C. under reduced pressure, to give 2, as a light tan powder, m.p.: above 280 C.

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Cinnoline-4-carboxylic acid, A common heterocyclic compound, 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.”21905-86-2

EXAMPLE 5 n-Propyl Cinnoline-4-carboxylate (5) A suspension of 870 mg of 1, and 850 mg of carbonyidimidazole (CDII) in 30 ml of tetrahydrofuran (THF) was stirred at room temperature until CO2 evolution ceased (ca. 30 minutes). After being stirred for 2 hours, the resulting mixture was treated with 320 mg of dry nypropanol and 3 drops of a 0.1 M solution of sodium imidazole in THE. The mixture was held at room temperature overnight, then the solvent was evaporated and the residue was partitioned between water and ether. The etheral extract was washed with saturated sodium bicarbonate solution, then with brine, then dried (MgSO4) and stripped in a rotary evaporator. The residue was chromatographed over silica gel, using a 1:1 v:v mixture of cyclohexane and ethyl acetate as eluent, to give 5, as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis, Cinnoline-4-carboxylic acid, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2, A common heterocyclic compound, 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.”21905-86-2

A solution of cinnoline-4-carboxylic acid (183 mg, 1.02 mmol) in methylene chloride (20 ml) was reacted with EDCI (195 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 min and then stirred, together with 4b-amino-9b-hydroxy-7-isopropyl-4b,9b-dihydro-5-oxa-indeno[2,1-a]-inden-10-one (250 mg, 0.85 mmol), overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO4 and concentrated in a vacuum. Purification by column chromatography (ethylacetate:n-hexane=1:1) afforded the title compound as a white solid (290 mg, 63%). [0846] 1H-NMR (300 MHz, CD3OD) delta 1.15 (d, J=6.8 Hz, 6H, CH3), 2.82 (sep, J=6.8 Hz, 1H, CH), 6.69 (s, 1H, ArH), 6.89 (d, J=7.8 Hz, 1H, ArH), 7.45 (d, J=7.9 Hz, 1H, ArH), 7.65 (m, 1H, ArH), 7.858.03 (m, 5H, ArH) 8.42 (d, J=8.0 Hz, 1H, ArH), 8.51 (d, J=8.4 Hz, 1H, ArH), 9.45 (s, 1H, ArH).

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN K.U. LEUVEN R & D; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Jung, Young Sik; Lee, Chong Kgo; Kim, Hae Soo; Jeong, Hee Chun; Kim, Pil Ho; Han, Soo Bong; Shin, Jin Soo; Neyts, Johan; Thibaut, Hendrik Jan; US2014/114068; (2014); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics