Category: cinnoline

New Advances in Chemical Research, April 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.3-Bromocinnoline,which mentioned a new discovery about 78593-33-6. 78593-33-6

(a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of 3-bromocinnoline, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50 ml of dimethylsulphoxide was stirred and heated at 120 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield: 10.2%

A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 78593-33-6., 78593-33-6

Reference：
Patent; Sanofi; US4994474; (1991); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

New Advances in Chemical Research, April 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.Cinnoline-4-carboxylic acid,which mentioned a new discovery about 21905-86-2. 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).

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.21905-86-2, you can also check out more blogs about21905-86-2

Reference：
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

New research progress on 21905-86-2 in 2021. 21905-86-2,In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. In an article, Which mentioned a new discovery about21905-86-2 Name is Cinnoline-4-carboxylic acid.

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)., 21905-86-2

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Reference：
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

New Advances in Chemical Research, April 2021.78593-33-6. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. Introduce a common compound, CAS is 78593-33-6, Name is 3-Bromocinnoline, belongs to cinnolinecompound.

Starting material 1-A (11.8 g, 40 mmol), starting material 1-B (16.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.1 g, 80 mmol), and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring under a nitrogen atmosphere for 7 days. Then, the reaction mixture was cooled to room temperature, 300 ml of water was added to isolate the organic layer, and the water layer was extracted twice with 250 ml of dichloromethane. The extracted organic layer was stirred with MgSO4 to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The resulting solid was subjected to column chromatography using, as an eluent, dichloromethane and normal hexane to obtain 5.6 g of Intermediate 1-C at the yield of 33%. MS (MALDI-TOF) m/z: 424 [M]+

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Reference：
Patent; SAMSUNG DISPLAY CO., LTD.; Kim, Myeongsuk; Ye, Jimyoung; Yoo, Byeongwook; Cho, Illhun; Kang, Sunwoo; Kim, Sunjae; Jeong, Jaeho; (112 pag.)US2020/99001; (2020); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

New Advances in Chemical Research, April 2021.78593-33-6. Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media. Introduce a common compound, CAS is 78593-33-6, Name is 3-Bromocinnoline, belongs to cinnolinecompound.

78593-33-6, Using the same procedure as that described above but from 3-bromocinnoline there was obtained 3-(4-methoxyphenylthio)cinnoline Yield: 74.6% M.P.: 108 C. (isopropanol)

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.78593-33-6, you can also check out more blogs about78593-33-6

Reference：
Patent; Sanofi; US4994474; (1991); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

New Advances in Chemical Research, April 2021.875-66-1. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. Introduce a common compound, CAS is 875-66-1, Name is Cinnolin-4-ol, belongs to cinnolinecompound.

Example 20: Synthesis of 1- [4- (5-FLUORO-2-METHOXYPHENYL)-2-HYDROXY-4-METHYL-2- TRIFLUOROMETHYLPENTYL]-LH-CINNOLIN-4-ONE To a suspension of 2- [2- (5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (216 mg) and cinnolin-4-ol (V. G. Chapoulaud et AL., Tetrahedron, 2000,56, pp. 5499-5507) (216 mg) in anhydrous ethanol (1.2 ML) was added sodium ethoxide (21 wt. % solution in ethanol, 276 PL). After heating at 85C for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (26 mg), m. p. 122C-123C.

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Reference：
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

New research progress on 21905-86-2 in 2021. 21905-86-2,In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. In an article, Which mentioned a new discovery about21905-86-2 Name is Cinnoline-4-carboxylic acid.

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.

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.21905-86-2, you can also check out more blogs about21905-86-2

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

New Advances in Chemical Research, April 2021.875-66-1. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. Introduce a common compound, CAS is 875-66-1, Name is Cinnolin-4-ol, belongs to cinnolinecompound.

Example 20: Synthesis of 1- [4- (5-FLUORO-2-METHOXYPHENYL)-2-HYDROXY-4-METHYL-2- TRIFLUOROMETHYLPENTYL]-LH-CINNOLIN-4-ONE To a suspension of 2- [2- (5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (216 mg) and cinnolin-4-ol (V. G. Chapoulaud et AL., Tetrahedron, 2000,56, pp. 5499-5507) (216 mg) in anhydrous ethanol (1.2 ML) was added sodium ethoxide (21 wt. % solution in ethanol, 276 PL). After heating at 85C for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (26 mg), m. p. 122C-123C.

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Reference：
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

New Advances in Chemical Research, April 2021.875-66-1. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. Introduce a common compound, CAS is 875-66-1, Name is Cinnolin-4-ol, belongs to cinnolinecompound.

875-66-1, To a suspension of NaH (60% in mineral oil, 0.099 g, 2.46 mmol) in DMF (5 mL) was added cinnolin-4-ol (prepared from 2-aminoacetophenone according to the procedures described in U. S. Patent No. 4,620, 000), 0. 300 g, 2.05 mmol) in DMF (2 mL) dropwise. The reaction mixture was warmed at 40 C and stirred for 30 minutes. After cooling, N-phenyltrifluoromethanesulfonimide (0.880 g, 2.46 mmol) in DMF (2 mL) was added, and the reaction mixture was stirred at room temperature for 1 hour. 1-Boc piperazine (0.765 g, 4.11 mmol) was added to the mixture. The reaction was stirred at 80 C for 4 hours. After cooling, the mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated. The residue was purified by column chromatography (1: 1 to 1: 3 hexanes/EtOAc) to give 4- Cinnolin-4-yl-piperazine-l-carboxylic acid tert-butyl ester (0.246 g, 38%) as a yellow oil. 1H NMR (CDC13, 400 MHz) 8 8. 91 (s, 1H), 8. 47 (d, J= 8.4 Hz, 1H), 7.97 (d, J= 8. 4 Hz, 1H), 7.80 (t, J= 7.2 Hz, 1H), 7.69 (t, J= 7.2 Hz, 1H), 3.74 (m, 4H), 3. 34 (m, 4H), 1.51 (s, 9H). LCMS (APCI+) tnlz 315 [M+H]’ ; Rt = 2.14 minutes.

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Reference：
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

New Advances in Chemical Research, April 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.Cinnoline-4-carboxylic acid,which mentioned a new discovery about 21905-86-2. 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).

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Reference：
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