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, 3-c]quinolin-5-yl)oxy)methyl)piperidin-1-yl)ethyl)-2,3-dihydro1H-isoindole-1,3-dione 13a, vol.2, pp.3-4
, 3-c]quinolin-5-yl)oxy)methyl]piperidine-1-carboxylate 10 (900 mg, 1.73 mmol) and following the general procedure A. The crude product was dissolved in acetonitrile (50 mL) and N-(2-bromoethyl)phthalimide (526 mg, 2.08 mmol) and triethylamine (0.45 mL, 3.50 mmol) were added. The solution was stirred at 80°C for 24 hours and the white precipitate formed was filtered, vol.2
, 3-c]quinolin-5-yl)oxy)methyl)piperidin-1-yl)propyl)-2,3-dihydro1H-isoindole-1, vol.2, pp.3-13
, mmol) and following the general procedure A. The crude product was dissolved in acetonitrile (20 mL) and N-(3-bromopropyl)phthalimide (185 mg, 0.70 mmol) and triethylamine (0.19 mL, 1.4 mmol) were added. The solution was stirred at 80°C for 12 hours and the white precipitate formed was filtered, vol.2
, 3-c]quinolin-5-yl)oxy)methyl)piperidin-1-yl)butyl)-2,3-dihydro1H-isoindole-1, vol.2, pp.3-13
, mmol) and following the general procedure A. The crude product was dissolved in acetonitrile (20 mL) and N-(4-bromopbutyl)phthalimide (240 mg, 0.85 mmol) and triethylamine (0.19 mL, 1.4 mmol) were added. The solution was stirred at 80°C for 24 hours and the white precipitate formed was filtered, vol.2
, quinolin-5-yl)oxy)methyl)piperidine-1-yl)butyl)-2,3dihydro-1H-isoindole-1,3-dione (225 mg, 0.44 mmol) 31b and following the general procedure B. The crude product was dissolved in dichloromethane (10 mL) and dansyl chloride (113 mg, 0.42 mmol) and triethylamine (0.12 mL, 0.90 mmol) were added. The solution was stirred at room temperature for 15 minutes. The organic layer was washed with water (15 mL), extracted with dichloromethane (2 x 15 mL), dried over MgSO 4 , filtrated and evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol, pp.2-3
01 (d, 3 J = 2.0 Hz, 1H), 400 MHz, CDCl 3 ): ? = 9.08 (d, 3 J = 2.0 Hz, 1H), vol.9 ,
, Hz, 1H), 7.53-7.47 (m, 3H), 7.16 (dd, 3 J = 7.6 Hz, 4 J = 0.8 Hz, 1H), vol.4, p.67
, 100 MHz, CDCl 3 ): ? = 158.4, 157.1 (d, J = 253 Hz), 151.9, 147.9, 145.7 (d, J = 4 Hz), 145.4, 135.9, vol.133
, quinolin-5-yl)oxy)methyl)piperidine-1-yl)hexyl)-2,3dihydro-1H-isoindole-1,3-dione (145 mg, 0.27 mmol) 31c and following the general procedure B. The crude product was dissolved in dichloromethane (7 mL) and dansyl chloride (62 mg, 0.23 mmol) and triethylamine (0.07 mL, 0.54 mmol) were added. The solution was stirred at room temperature for 15 minutes. The organic layer was washed with water (10 mL), extracted with dichloromethane (2 x 10 mL), dried over MgSO 4 , filtrated and evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol, pp.2-3
02 (d, 3 J = 2.0 Hz, 1H), 8.70-8.65 (m, 1H), 8.56-8.51 (m, 1H), 8.30-8.36 (m, 1H), 8.24 (dd, 3 J = 7.3 Hz, 4 J = 1.3 Hz, 1H), 400 MHz, CDCl 3 ): ? = 9.08 (d, 3 J = 2.0 Hz, 1H), vol.9 ,
, 100 MHz, CDCl 3 ): ? = 158.4, 157.0 (d, J = 254 Hz), 152.2, 147.9, 145.7 (d, J = 4 Hz), vol.133
, CDCl 3 ): ? =-126.0 (t
, Tert-butyl N-(2-iodophenyl)carbamate 39b
, mmol), and following the general procedure G. The residue was purified by silica gel chromatography using petroleum ether/diethylether (90/10) as eluent affording the expected product as a white solid (180 mg
CDCl 3 ): ? = 8.05 (dd, J = 8.3 Hz, J = 1.6 Hz, 1H), 7.40 (dd, J = 8.0 Hz, MHz, vol.1, issue.400 ,
, Hz, 1H), 7.31 (td, J = 7.8 Hz, J = 1.6 Hz, 1H), 6.82 (bs, 1H)
, MHz, issue.100
, Org. Lett, vol.16, pp.3240-3243, 2014.
, mg, 1.34 mmol), and following the general procedure G. The residue was purified by silica gel chromatography using petroleum ether/diethylether (90/10) as eluent affording the expected product as a white solid (336 mg, vol.1, p.22
, Iodophenyl)benzamide 39f
, Starting from N-phenylbenzamide (200 mg, 1.01 mmol), and following the general procedure G. The residue was purified by silica gel chromatography using petroleum ether/diethylether (80/20) as eluent affording the expected product as a white solid (210 mg
, CDCl 3 ): ? = = 8.46 (dd, J = 8.3 Hz, J = 1.6 Hz 1H), 8.30 (bs, 1H), m, 2H), 7.82 (dd, J = 7.9 Hz, J = 1.5 Hz, 1H
, Hz, J = 1.6 Hz, 1H)
CDCl 3 ): ? = 165, MHz, vol.4, issue.100 ,
, Tetrahedron Lett, vol.56, pp.2167-2171, 2015.
, fluorophenyl)pyrazine 46 (2.40 g, 9.71 mmol), Pyrazino[2,3-c]quinolin5(6H)-one was prepared according to the literature procedure and was obtained as a white solid, vol.2, p.75
, 400 MHz, DMSO-d 6 ): ? = 12.10 (br s, 1H), vol.9
, , p.51
, quinolin-5-yl)oxy)methyl)piperidine-1-carboxylate (50 mg, 0.13 mmol) and palladium acetate (29 mg, 0.13 mmol) was dissolved in acetonitrile (1 mL). The mixture was stirred a room temperature for 4 hours and filtrated. The precipitate was washed with acetonitrile
CDCl 3 ): ? = 8.57 (d, 3 J = 2.6 Hz, 1H), MHz, vol.8, issue.400 ,
,
, MHz, CDCl, vol.376, issue.5
, Hydrazine monohydrate (0.73 mL, 15 mmol) was added and the solution was stirred under reflux until the solubilisation of the mixture. Ethanol was evaporated and the residue was dissolved in dichloromethane (20 mL) at 0°C, filtered and concentrated under reduced pressure. The primary amine was dissolved in dichloromethane (20 mL) and the solution was cooled down to 0°C. Triethylamine (0.1 mL, 1.2 mmol) and methanesulfonyl chloride (0.05 mL, 0.7 mmol) were added to the solution and the mixture was stirred 5 min at 0°C and 5 min at room temperature, A round bottom flask was filled with 51 (520 mg, 0.45 mmol) and NIS (221 mg, 0.98 mmol) in dichloromethane (25 mL)
CDCl 3 ): ? = 9, MHz, vol.8, issue.400 ,
, Hz, 1H), 7.19 (t, J = 8.9 Hz, 1H)
, 100 MHz, CDCl 3 ): ? = 157.7, 157.7 (d, J = 254 Hz), vol.140
, CDCl 3 ): ? =-124.0 (dd, J = 9.6 Hz, J =, vol.5
, mmol) and following the general procedure A. The crude product was then dissolved in acetonitrile (10 mL) and N-(2-bromoethyl)phthalimide (110 mg, 0.44 mmol) and triethylamine (0.10 mL, 0.72 mmol) were added. The solution was stirred at 80°C for 24 hours and the white precipitate formed was filtered, washed with acetonitrile (2 x 10 mL). The precipitate was dissolved in ethanol (15 mL) and following the general procedure B. The primary amine was dissolved in dichloromethane (10 mL) and the solution was cooled down to 0°C. Triethylamine (0.10 mL, 0.72 mmol) and methanesulfonyl chloride (0.02 mL, 0.30 mmol) were added to the solution and the mixture was stirred 5 min at 0°C and 5 min at room temperature. The organic layer was washed with water (15 mL), dried over MgSO 4 , filtrated and evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol, vol.2
02 (d, 3 J = 2.0 Hz, 1H), 8.71-8.64 (m, 1H, 400 MHz, CDCl 3 ): ? = 9.09 (d, 3 J = 2.0 Hz, 1H), vol.9 ,
CDCl 3 ): ? =-126 ,
, 48 mmol) and following the general procedure A. The crude product was then dissolved in acetonitrile (15 mL) and N-(2-bromoethyl)phthalimide (144 mg, 0.58 mmol) and triethylamine (0.13 mL, 0.96 mmol) were added. The solution was stirred at 80°C for 24 hours and the white precipitate formed was filtered, washed with acetonitrile (2 x 10 mL). The precipitate was dissolved in ethanol (20 mL) and following the general procedure B. The primary amine was dissolved in dichloromethane (15 mL) and the solution was cooled down to 0°C. Triethylamine (0.13 mL, 0.96 mmol) and methanesulfonyl chloride (0.03 mL, 0.41 mmol) were added to the solution and the mixture was stirred 5 min at 0°C and 5 min at room temperature. The organic layer was washed with water (15 mL), dried over MgSO 4 , filtrated and evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol, vol.2
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