Day: September 7, 2020

A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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. 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)

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

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

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

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21905-86-2,Cinnoline-4-carboxylic acid,its application will become more common.

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
Cinnoline – an overview | ScienceDirect Topics

A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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. 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)

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

Reference£º
Patent; Sanofi; US4957925; (1990); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

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

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.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21905-86-2,Cinnoline-4-carboxylic acid,its application will become more common.

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

A common heterocyclic compound, 875-66-1,Cinnolin-4-ol, 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. 875-66-1

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.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,875-66-1,Cinnolin-4-ol,its application will become more common.

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

875-66-1 A common heterocyclic compound, 875-66-1,Cinnolin-4-ol, 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.

(0509) Compound 110 (292 mg, 2.00 mmol) was refluxed in POCl3 overnight. It was cooled to room temperature and poured into ice water, neutralized with Na2C03. The precipitation was filtered out and washed with water, dried by pulling air through. Product was obtained as light yellow solid. (0510) (243mg, 74%). 1H NMR (400 MHz, chloroform-i/) delta 9.35 (s, 1H), 8.57 (ddd, J= 8.5, 1.4, 0.7 Hz, 1H), 8.20 (ddd, J= 8.2, 1.6, 0.7 Hz, 1H), 7.97 – 7.83 (m, 2H).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,875-66-1,Cinnolin-4-ol,its application will become more common.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; YIN, Hang Hubert; ZHANG, Shuting; HU, Zhenyi; (114 pag.)WO2019/89648; (2019); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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. 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%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

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

A common heterocyclic compound, 875-66-1,Cinnolin-4-ol, 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. 875-66-1

Cinnolin-4(1H)-one (5.0 g, 34.24 mol) was added to the K2CO3 ( 7.08 g, 51.36 mol) and 3- bromoprop-1-yne (3.11 mL, 41.09 mol) in ACN (20 mL) and the mixture stirred at 80 C for 4-8 h then reaction mixture was cool to rt. The mixture was concentrated, diluted with H2O (30 mL), and extracted with EtOAc (3 ¡Á 50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. Flash chromatography gave 4-(prop-2-yn-1-yloxy)cinnoline (13a). Synthesis of 4-(prop-2-yn-1-yloxy)cinnoline (4a). Yield (2.60 g, 65.5%). m.p. 100-110 C. Colourless solid.1H NMR (400 MHz, CDCl3) delta 8.34 (dd, J = 1.2, 1.2 Hz, 1H, Ar), 7.81-7.77 (m, 2H, Ar), 7.60 (d, J = 8.8 Hz, 1H, Ar), 7.46 (t, J = 8.0 Hz,1H, Ar), 5.14 (d, J = 2.4 Hz, 1H, -OCH2), 2.51 (t, J = 2.4 Hz, 1H, Alky). 13C NMR (100 MHz, CDCl3) delta 171.2, 140.6, 140.1, 134.0, 126.0, 125.2, 124.6, 115.1, 76.0, 75.7, 46.2. ESI-MS: m/z 185.27 [M+H]+. Anal. Calc. (C11H8N2O) C: 71.73; H: 4.38; N: 15.21. Found C: 71.80; H: 4.04; N: 15.28%.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,875-66-1,Cinnolin-4-ol,its application will become more common.

Reference£º
Article; Boda, Sathish Kumar; Bommagani, Mohan Babu; Chitneni, Prasad Rao; Mokenapelli, Sudhakar; Yerrabelli, Jayaprakash Rao; Synthetic Communications; (2020);,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

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

To a solution OF 4- [ (Z)- (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), cinnoline-4-carboxylic acid (25mg, 0.14 mmol), Et3N (0.06 mL, 0.43 MMOL) in DMF (3 mL, anhydrous) was added HATU (60mg, 0. 16MMOL) at room temperature. After 16 h the reaction mixture was poured into ice water, and the solid was collected by filtration. The solid was dissolved in CH2CI2, and dried over NA2SO4. Concentration in vacuo, and purification by preparative TLC (CH2CI2-MEOH, 9: 1) afforded the title compound as a light yellow powder. MS: 564 (M+).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,Cinnoline-4-carboxylic acid,21905-86-2,its application will become more common.

Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics