Heterocyclic Building Blocks-Cinnoline

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EXAMPLE 63f Synthesis of Cinnoline-4-carboxylic acid [2-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide (Compound 63f) The procedure in Example 63d step 3 was followed using cinnoline-4-carboxylic acid. The reaction was stirred at RT for 1 day and at reflux for 1 day. Purification by chromatography (SiO2, 5-8% MeOH/CH2Cl2 with 1% NH4OH) afforded the title compound as a foam (63 mg, 0.125 mmol, 44%). The structure was confirmed by NMR and mass spectrometry. MS m/z 505 (M++H).

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Reference£º
Patent; Denny, William Alexander; Hutchings, Richard H; Johnson, Douglas S; Kaltenbronn, James Stanely; Lee, Ho Huat; Leonard, Daniele Marie; Milbank, Jared Bruce John; Repine, Joseph Thomas; Rewcastle, Gordon William; White, Andrew David; US2004/44057; (2004); A1;,
Cinnoline – Wikipedia
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875-66-1,The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.Cinnolin-4-ol,which mentioned a new discovery about 875-66-1.

a. 4-Chloro-8-nitroquinoline (6a). This intermediate was prepared from 4-chloroquinoline (obtained by treating 4-hydroxyquinoline with [POC13] as [ DESCRIBED BY GOULEY, R. W., ET AL. , J. AMER. CHEM. SOC., 1947, 69, 303-306.4-] Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below 15 C. Then the solution was cooled and maintained at-15 C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 hours. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g of 6a, in 59 % yield; m. p. = [128-129 C] (lit. m. p. = [129-130 C) ; IH] NMR [(CDC13)] [8] 7.67 (d, [1H,] J=4. 5), 7.75 (dd, 1H, J=8. 6 [HZ,] J=7. 6), 8.10 (dd, 1H, J=7. 6, J=1. 3), 8. 48 (dd, 1H,. [J=8.] [6,] J=1.3), 8.94 (d, 1H, J=4. 5); [13C] NMR [(CDC13)] [8] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1.

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Reference£º
Patent; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2,Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.Which mentioned a new discovery about21905-86-2 .

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.

Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. I hope my blog about 21905-86-2 is helpful to your research. 21905-86-2

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

21905-86-2,Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 21905-86-2,introducing its new discovery.

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£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

318276-74-3,Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 318276-74-3,introducing its new discovery.

A solution of the compound from example 3d) (345 mg; 1.8 mmol.) in anhydrous tetrahydrofuran (20.0 mL) was cooled to 5 oC for the portionwise addition of solid lithium aluminumhydride (70.0 mg; 1.8 mmol.) and stirred at 5 0C for 1 h. The mixture was quenched by the addition of ethyl acetate (50.0 mL) then water (5.0 mL), filtered through a pad of Celite and evaporated. The residue was dissolved in ethyl acetate (50.0 mL) and treated with manganese dioxide (0.50 g) and stirred at room temperature for 2 h. The mixture was filtered through a pad of Celite and evaporated to afford the title EPO compound (169 mg; 60%) as a brown powder which was used directly in the following step without further purification,

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Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/38331; (2007); A2;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, get their minds active, and encourage them to do something that doesn¡¯t involve a screen. 21905-86-2, 21905-86-2,introducing its new discovery.

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.

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

One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, such as the rate of change in the concentration of reactants or products with time. 21905-86-2, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 21905-86-2, name is C9H6N2O2. In an article£¬Which mentioned a new discovery about 21905-86-2

EXAMPLE 42 2-(2-ethoxyethoxy)ethyl cinnoline-4-carboxylate (42) 1.07 g of CDIT was added to a mixture of 1.04 g of 1 in 70 ml of dry THF under nitrogen, the mixture was stirred at room temperature for 4 hours, 1.6 g of 2-(2-ethoxyethoxy)ethanol and 0.032 g of sodium methoxide were added and the mixture was stirred at room temperature over a weekend. Then the solvent was stripped, and the residue was dissolved in methylene chloride. The solution was washed with water, dried (MgSO4) and stripped of solvent. The residue was flash-chromatographed on silica gel, using a 1:4 v:v mixture of ethyl acetate and methylene chloride as eluent, to give 42, as a yellow oil., 21905-86-2

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

38024-35-0,Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 38024-35-0,introducing its new discovery.

To a suspension of 4-aminocinnoline-3-carboxamide (3.5 g, 18.60 mmol) in DCM (10 ml) was added POCI3 (43.3 ml, 465 mmol) followed by triethylamine (7.78 ml, 55.8 mmol). The mixture was refluxed for 7 h. The reaction was then allowed to cool to 11 and conc, in vacuo. The crude residuewas then carefully treated with saturated aqueous NaHCO3 at 0 C. A precipitate formed which was collected via vacuum filtration. The filter cake washed with water (-i00 ml,), collected, and driedvacuo to provide the title compound as a grey solid 4-aminocinnoiine-3-carbonitriie.

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Reference£º
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.3-Bromocinnoline,which mentioned a new discovery about 78593-33-6. 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).

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Reference£º
Patent; Sanofi; US5017579; (1991); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

78593-33-6,Chemistry, like all the natural sciences, begins with the direct observation of nature¡ª in this case, of matter.Which mentioned a new discovery about 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%.

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Reference£º
Patent; Sanofi; US5017579; (1991); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics