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[ CAS No. 124467-36-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 124467-36-3
Chemical Structure| 124467-36-3
Chemical Structure| 124467-36-3
Structure of 124467-36-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 124467-36-3 ]

CAS No. :124467-36-3 MDL No. :MFCD08692066
Formula : C9H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :GWDDFDLEOYOZLY-UHFFFAOYSA-N
M.W : 181.62 Pubchem ID :592839
Synonyms :

Calculated chemistry of [ 124467-36-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.1
TPSA : 29.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 1.35
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.11

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.495 mg/ml ; 0.00273 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 1.14 mg/ml ; 0.00625 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.64
Solubility : 0.0418 mg/ml ; 0.00023 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.09

Safety of [ 124467-36-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P273-P280-P305+P351+P338 UN#:1759
Hazard Statements:H302-H315-H318-H335-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 124467-36-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 124467-36-3 ]

[ 124467-36-3 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 124467-36-3 ]
  • [ 124467-37-4 ]
YieldReaction ConditionsOperation in experiment
64% With hydrogen bromide; bromine; In dichloromethane; at 20℃; To a solution of <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (2 g, 11.2 mmol) in HBr (20 mL)was added Br2 (1.79 g, 11.2 mmol) in DCM (20 mL) at RT and stined for 2 h at the sametemperature. The reaction was quenched with ice-water, extracted with ethyl acetate. The organic portion was dried over anhydrous sodium sulphate, filtered and concentrated to get the title compound (1.8 g, 64%). LC-MS: 260.1 [M], 262.1 [M+2H].
With bromine; potassium carbonate; In chloroform; The latter compound (2 g) was dissolved in chloroform (200 ml) and treated with bromine (0.53 ml) dropwise at room temperature. After 30 min solid potassium carbonate was added, the mixture was stirred for 1 hour, filtered and solvent removed to give 2-chloro-6-bromo-7,8-dihydro-5-quinolinone (2.86 g).
  • 2
  • [ 124467-36-3 ]
  • [ 536-74-3 ]
  • [ 864224-08-8 ]
YieldReaction ConditionsOperation in experiment
15% With triethylamine;tetrakis(triphenylphosphine) palladium(0); for 3h;Heating / reflux; To a solution of <strong>[124467-36-3]2-chloro-7,8-dihydro-6H-quinolin-5-one</strong> (0.2 g, 1.1 mmol) and ethynylbenzene (0.17 g, 1.6 mmol) in triethylamine (7 ml) under an argon atmosphere was added tetrakis (triphenylphosphine) palladium (0.02 g, 0.062 mmol). The mixture was heated at reflux for 3 h. Then it was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give the title compound (0.04 g, 15%). Physical characteristics are as follows:Mp 121-122 0C; 1H NMR (CDCI3, TMS) delta: 2.20 (2H); 2.68 (2H); 3.17 (2H);7.22-7.38 (3H); 7.46 (1H); 7.60 (2H); 8.24 (1 H); MS 248 (M+1).
15% With triethylamine;tetrakis(triphenylphosphine) palladium(0); for 3h;Heating / reflux; To a solution of <strong>[124467-36-3]2-chloro-7,8-dihydro-6H-quinolin-5-one</strong> (0.2 g, 1.1 mmol) and ethynylbenzene (0.17 g, 1.6 mmol) in triethylamine (7 ml) under an argon atmosphere was added tetrakis (triphenylphosphine) palladium (0.02 g, 0.062 mmol). The mixture was heated at reflux for 3 h. Then it was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give the title compound (0.04 g, 15%). Physical characteristics are as follows: Mp 121-122 0C; 1H NMR (CDCI3, TMS) delta: 2.20 (2H); 2.68 (2H); 3.17 (2H);7.22-7.38 (3H); 7.46 (1 H); 7.60 (2H); 8.24 (1 H); MS 248 (M+1 ).
15% tetrakis(triphenylphosphine)palladium (0); In triethylamine; EXAMPLE 1 2-Phenylethynyl-7,8-dihydro-6H-quinolin-5-one To a solution of <strong>[124467-36-3]2-chloro-7,8-dihydro-6H-quinolin-5-one</strong> (0.2 g, 1.1 mmol) and ethynylbenzene (0.17 g, 1.6 mmol) in triethylamine (7 ml) under an argon atmosphere was added tetrakis (triphenylphosphine) palladium (0.02 g, 0.062 mmol). The mixture was heated at reflux for 3 h. Then it was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give the title compound (0.04 g, 15%). Physical characteristics are as follows: Mp 121-122 C.; 1H NMR (CDCl3, TMS) delta: 2.20 (2H); 2.68 (2H); 3.17 (2H); 7.22-7.38 (3H); 7.46 (1H); 7.60 (2H); 8.24 (1H); MS 248 (M+1).
  • 3
  • [ 124467-36-3 ]
  • 1,3-diphenyl-1H-pyrazole-5-boronic acid [ No CAS ]
  • 2-(2,5-diphenyl-2H-pyrazol-3-yl)-7,8-dihydro-6H-quinolin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With triethylamine;tetrakis(triphenylphosphine) palladium(0); In toluene;Heating / reflux; 2-(2,5-Diphenyl-2H-pyrazol-3-yl)-7,8-dihydro-6H-quinolin-5-one[0095] To a solution of <strong>[124467-36-3]2-chloro-7,8-dihydro-6H-quinolin-5-one</strong> (0.2 g, 1.1 mmol) and 1 ,3-diphenyl-1 H-pyrazole-5-boronic acid (1.6 mmol) in triethylamine (7 ml) and toluene under an argon atmosphere was added tetrakis (triphenylphosphine) palladium (0.02 g, 0.062 mmol). The mixture was EPO <DP n="53"/>heated at reflux over night. Then it was concentrated under reduced-pressure and the residue was purified by column chromatography on silica gel to give the title compound (5 %).
  • 4
  • [ 1945-84-2 ]
  • [ 124467-36-3 ]
  • 2-pyridin-2-ylethynyl-7,8-dihydro-6H-quinolin-5-one [ No CAS ]
  • 5
  • [ 124467-36-3 ]
  • [ 92-54-6 ]
  • [ 864225-58-1 ]
  • 6
  • [ 15450-69-8 ]
  • [ 124467-36-3 ]
YieldReaction ConditionsOperation in experiment
96% With trichlorophosphate; In acetonitrile; at 75℃; for 1.25h;Inert atmosphere; Example 3A 2-Chloro-7,8-dihydroquinolin-5(6H)-one Under nitrogen, 21.02 g (0.13 mol) of 7,8-dihydroquinoline-2,5(1H,6H)-dione were suspended in 100 ml of acetonitrile (anhydrous, <30 ppm H2O), and 135.28 ml (density 1.46 g/ml, 1.29 mol) of phosphorus oxychloride were added. The yellowish suspension was then heated to 75 C. and stirred at this temperature for 1.25 hours. The yellow clear solution was then cooled to room temperature, and 150 ml of toluene were added. The solution was then concentrated on a rotary evaporator to about 100 ml, and another 150 ml of toluene were added. The solution was then concentrated to dryness on a rotary evaporator. 300 ml of ethyl acetate were then added to the orange oil obtained. Subsequently, the solution was carefully (evolution of gas) added to 500 ml of saturated aqueous sodium bicarbonate solution and stirred for 15 min. The phases were separated and the aqueous phase was extracted with 200 ml of ethyl acetate. The combined organic phases were washed twice with 250 ml of water and once with 100 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure. This gave 22.58 g (0.12 mmol, 96% of theory) of the target compound as a slightly yellowish solid. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 2.06-2.17 (m, 2H), 2.61-2.70 (m, 2H), 3.05 (t, 2H), 7.51 (d, 1H), 8.18 (d, 1H).
90.9% With trichlorophosphate; In acetonitrile; for 2h;Reflux; To a solution of 7,8-dihydroquinoline-2,5(1H,6H)-dione (5 g, 27.6 mmol ) in acetonitrile(50 mL) was added POC13 (12.6 g, 82.5 mmol) dropwise at 0 C. The cooling bath was removedand the reaction mixture was refluxed for 2h. The reaction mixture was cooled to room temperature and the volatiles were evaporated under reduced pressure to get the residue, which was neutralized with ammonium hydroxide and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to get the title compound (5 g, 90.9%).LC-MS: 181.9 [M+H].
74% 3.2 2-Chloro-7,8-dihydroquinolin-5(6H)-oneTo a suspension of 7,8-dihydroquinoline-2,5(1H,6H)-dione (1.5 g, 9.19 mmol) in acetonitrile (22 mL) was added dropwise phosphorous oxychloride (1.714 mL, 18.39 mmol). The resulting solution was heated to 100 C. and stirred for 2 h. The reaction was cooled to RT and poured into ice-cold water. After basifying the mixture with 2 M sodium hydroxide solution it was extracted with ethyl acetate (3×). After each extraction the pH of the aqueous phase was checked and if necessary adjusted by adding 1 M sodium hydroxide solution. The combined organic layers were dried over sodium sulfate, filtered, and evaporated to dryness. The crude was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate) yielding a colourless solid. Amount 1.23 g. Yield 74%.1H-NMR (DMSO-d6, 400 MHz) delta 2.13 (m, 2H), 2.68 (m, 2H), 3.08 (t, 2H), 7.53 (d, 1H), 8.20 (d, 1H)MS (ES-API) m/z 182.0 (M+H+, 100%).
66% With trichlorophosphate; at 90℃; for 0.666667h; Example 7 (+-)-[2-(2,6-Diethyl-phenyl)-5,6,7,8-tetrahydro-quinolin-5-yl]-ethyl-naphthlen-1-yl-amine (Compound #109) 7,8-Dihydro-1H,6H-quinoline-2,5-dione (101 mg, 0.621 mmol, 1 equiv) was treated with POCl3 (1.0 mL, 10.9 mmol, 18 equiv) and the resulting suspension was heated in a 90 C. oil bath for 40 minutes. The resulting mixture was concentrated and the residue was poured into ice (5 mL). The resulting suspension was neutralized to pH 7 by addition of solid Na2CO3 and was extracted with CH2Cl2 (3*5 mL). The organic phase was washed with water (15 mL), then was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (SiO2, 0-20% EtOAc in hexanes) to yield 2-chloro-7,8-dihydro-6H-quinolin-5-one as a white solid (74.3 mg, 66%). 1H NMR (300 MHz, CDCl3) delta 8.23 (d, 1H), 7.31 (d, 1H), 3.14 (t, 2H), 2.69 (t, 2H), 2.20 (quint, 2H); MS m/z (MH+) 182.1.
To 200 mg (1.23 mmol) of 7,8-dihydroquinoline-2,5(1H,6H)-dione in acetonitrile (6.1 mL) was added 1.14 mL (12.3 mmol) of phosphorous oxychloride and the mixture was heated at 65 C. for 3 hours. The reaction was cooled to room temperature and the excess phosphorous oxychloride was removed via rotary evaporation. The residue was partitioned between EtOAc (400 mL) and water (200 mL) and the organic phase was washed sequentially with saturated NaHCO3 (200 mL) and brine (200 mL). The organic phase was dried over MgSO4 and concentrated to afford N-1 as a beige solid. Data for N-1: LC/MS: rt=1.64 min; m/z (M+H)=182.1 found; 182.0 required.
630 mg With trichlorophosphate; In acetonitrile; at 100℃; for 3h; Step 2: 2-Chloro-7,8-dihydro-6H-quinolin-5-one. 7,8-Dihydro-1 H,6H-quinoline-2,5-dione (1 .1 g, 6.74 mmol) is dissolved in acetonitrile (25 ml), phosphorus oxychloride (1 .26 ml, 13.5 mmol) is added dropwise and the mixture is stirred at 100C for 3 hours. The mixture is cooled to 0C and poured into cold water, NaOH 2M aq. solution is added until pH >7 is reached, then the mixture is extracted with dichloromethane (3 x 30 ml), the combined organic layers are dried over sodium sulphate, filtered and concentrated. The residue is purified by flash chromatography (0 - 20% ethyl acetate in cyclohexane) to give the title compound (Yield 630 mg). LC (Method 1 ): tR = 2.61 min; Mass spectrum (ES+): m/z = 182 [M+H]+.
13 g With trichlorophosphate; In acetonitrile;Reflux; S8. 20 g of compound P16015-2 was added to 200 mL+, and 98 g of phosphorus oxychloride was added dropwise to the reaction solution through a constant pressure dropping funnel; after the dropwise addition was completed, the temperature was raised to reflux, and the reaction was stirred overnight. After completion of the reaction, the mixture was concentrated under reduced vacuo.S9. The organic phase is washed with a saturated aqueous solution of sodium carbonate to a weak basic. The organic phase was washed three times with a saturated aqueous solution of sodium chloride and then evaporated.S10. The crude solid was recrystallized using EA/PE = 1:2 solvent system to give a solid. Solid product using vacuum dried soil Yellow product 13g

  • 7
  • [ 124467-36-3 ]
  • [ 610286-39-0 ]
  • [ 1119227-47-2 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 28h;Heating / reflux; To a mixture of <strong>[124467-36-3]2-chloro-7,8-dihydro-6H-quinolin-5-one</strong> (68.8 mg, 0.379 mmol, 1 equiv), 2,6-diethylphenylboronic acid (70.8 mg, 0.398 mmol, 1.05 equiv) and Pd(PPh3)4 (21.9 mg, 18.9 mumol, 0.05 equiv) was added 2 M aqueous Na2CO3 (1 mL) and toluene (1 mL). The resulting mixture was heated at reflux under nitrogen for 1 d. Analysis of a sample of the reaction mixture by LCMS indicated incomplete conversion, so additional portions of 2,6-diethylphenylboronic acid, Pd(PPh3)4, 2 M aqueous Na2CO3, and toluene (amounts as above) were added and the resulting mixture was heated at reflux for an additional 4 h. The mixture was then partitioned between EtOAc (20 mL) and water (20 mL). The separated aqueous phase was extracted with two additional 20-mL portions of EtOAc. The organic extracts were dried (Na2SO4) and filtered, and the filtrate was concentrated. The resulting residue was purified by flash column chromatography (SiO2, 0-20% EtOAc in hexanes) to yield 2-(2,6-diethyl-phenyl)-7,8-dihydro-6H-quinolin-5-one (75.1 mg, 71%). 1H NMR (300 MHz, CDCl3) delta 8.34 (d, 1H), 7.23-7.34 (m, 2H), 7.15 (d, 2H), 3.21 (t, 2H), 2.75 (t, 2H), 2.33 (q, 4H), 2.26 (quint, 2H), 1.05 (t, 6H); MS m/z (MH+) 280.3.
  • 8
  • [ 124467-36-3 ]
  • [ 1241496-36-5 ]
  • 9
  • [ 124467-36-3 ]
  • C22H25ClN2O2 [ No CAS ]
  • 10
  • [ 124467-36-3 ]
  • C15H19ClN2O2 [ No CAS ]
  • 11
  • [ 124467-36-3 ]
  • C20H27ClN2O4 [ No CAS ]
  • C20H27ClN2O4 [ No CAS ]
  • 12
  • [ 124467-36-3 ]
  • C18H23ClN2O4 [ No CAS ]
  • 13
  • [ 124467-36-3 ]
  • C18H22Cl2N2O3 [ No CAS ]
  • 14
  • [ 124467-36-3 ]
  • C35H46ClN3O3 [ No CAS ]
  • 15
  • [ 124467-36-3 ]
  • C36H49N3O3 [ No CAS ]
  • 16
  • [ 124467-36-3 ]
  • [ 867-13-0 ]
  • C13H14ClNO2 [ No CAS ]
  • C13H14ClNO2 [ No CAS ]
  • 18
  • [ 124467-36-3 ]
  • [ 61394-50-1 ]
  • 2-Hydroxy-3-(5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)-1H-indole-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With sodium hexamethyldisilazane; In tetrahydrofuran; at 110℃; for 0.166667h;Microwave irradiation; 3.3 2-Hydroxy-3-(5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)-1H-indole-5-carbonitrileTo a suspension of <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (50 mg, 0.275 mmol) and 2-oxoindoline-5-carbonitrile (45.7 mg, 0.289 mmol) in tetrahydrofuran (1.4 mL) was added a 1.0 M solution of sodium bis(trimethylsilyl)amide (641 muL, 0.641 mmol). The mixture was stirred for 3 min at RT and then heated in a microwave oven to 110 C. for 10 min. After cooling to RT the reaction was quenched by addition of methanol (1 mL). The resulting solution was evaporated to dryness. The crude was purified by flash chromatography (silica gel, dichloromethane/methanol) yielding an orange solid. Amount 17 mg. Yield 20%.1H-NMR (DMSO-d6, 400 MHz) delta 2.17 (m, 2H), 2.59 (t, 2H), 3.08 (t, 2H), 7.06 (d, 1H), 7.38 (dd, 1H), 7.68 (d, 1H), 7.98 (m, 2H), 11.11 (s, 1H), 14.78 (bs, 1H)MS (ES-API) m/z 304 (M+H+, 100%).
  • 19
  • [ 124467-36-3 ]
  • [ 1429914-13-5 ]
  • 20
  • [ 124467-36-3 ]
  • [ 1429914-14-6 ]
  • 21
  • [ 124467-36-3 ]
  • [ 1429914-15-7 ]
  • 22
  • [ 124467-36-3 ]
  • 5-((1R,2S)-2-aminocyclohexylamino)-3-(5-methyl-7,8-dihydroquinolin-2-ylamino)picolinonitrile [ No CAS ]
  • 23
  • [ 124467-36-3 ]
  • [ 1429912-32-2 ]
  • 24
  • [ 124467-36-3 ]
  • [ 676-58-4 ]
  • [ 1429914-12-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 0℃; To a solution of <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (500 mg, 2.75 mmol) in tetrahydrofuran (20 mL) at 0C was added methylmagnesium chloride (3.0 M in tetrahydrofuran, 0.92 ml, 2.8 mmol) over 2 minutes dropwise. Additional methylmagnesium chloride (3.0 M in tetrahydrofuran) were added at the following time intervals after the initial addition: 40 minutes (0.46 ml, 1.4 mmol); 60 minutes (0.46 ml, 1.4 mmol); and 120 minutes (0.92 ml, 2.8 mmol). At 1 hour after the final addition, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 mL), and diluted with ethyl acetate (30 mL). The organic layer was separated and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (10-50% ethyl acetate/hexanes, linear gradient) to give 2-chloro-5-methyl-5,6,7,8-tetrahydroquinolin-5-ol. MS ESI calc'd. for C10H,3C1NO [M + H]+ 198, found 198.
  • 26
  • [ 557-21-1 ]
  • [ 124467-36-3 ]
  • [ 1471468-84-4 ]
YieldReaction ConditionsOperation in experiment
66% With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl acetamide; at 100℃; for 2h;Inert atmosphere; Example 4A 5-Oxo-5,6,7,8-tetrahydroquinoline-2-carbonitrile Under nitrogen, 42.25 g (0.23 mol) of <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong>, 54.64 g (0.47 mol) of zinc cyanide and 13.44 g (0.01 mol) of tetrakis(triphenylphosphine)palladium were suspended in 200 ml of anhydrous N,N-dimethylacetamide (water content <0.01%, degassed with nitrogen beforhand), heated to 100 C. and stirred at this temperature for 2 hours. After complete conversion (monitored by TLC, mobile phase petroleum ether/ethyl acetate 2:1), the reaction mixture (grey suspension) was cooled to room temperature and filtered through Celite, and the filter cake was washed with 500 ml of ethyl acetate. 200 ml of saturated aqueous sodium chloride solution were then added to the resulting organic solution. A white precipitate was formed, which was filtered off and discarded. The organic phase was separated off, washed three times with in each case 200 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness. The residue obtained was applied to 20 g of silica gel and purified by column chromatography on silica gel (80 g cartridge; flow rate: 60 ml/min; mobile phase: petroleum ether/ethyl acetate 95:5?60:40 over 40 min, then isocratic petroleum ether/ethyl acetate 60:40 for 30 min). This gave 26.35 g (0.15 mmol, 66% of theory) of the target compound. MS (EI): m/z=172 (M)+. 1H-NMR (400 MHz, CDCl3, delta/ppm): 2.19-2.30 (m, 2H), 2.70-2.79 (m, 2H), 3.20 (t, 2H), 7.67 (d, 1H), 8.39 (d, 1H).
  • 27
  • [ 124467-36-3 ]
  • [ 1542132-12-6 ]
  • 28
  • [ 124467-36-3 ]
  • ethyl 5-[2-(2-[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 29
  • [ 124467-36-3 ]
  • (-)-ethyl 5-{(5-ethoxy-5-oxopentyl)[2-(2-[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)-ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 30
  • [ 124467-36-3 ]
  • ethyl 5-[2-(2-[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 31
  • [ 124467-36-3 ]
  • rac-ethyl 5-[2-(2-[3-chloro-4'-(trifluoromethyl)-biphenyl-4-yl]methoxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 32
  • [ 124467-36-3 ]
  • [ 1542133-29-8 ]
  • 33
  • [ 124467-36-3 ]
  • [ 1542133-56-1 ]
  • 34
  • [ 124467-36-3 ]
  • [ 1542133-58-3 ]
  • 35
  • [ 124467-36-3 ]
  • [ 1542133-60-7 ]
  • 36
  • [ 124467-36-3 ]
  • [ 1542133-62-9 ]
  • 37
  • [ 124467-36-3 ]
  • [ 1542133-63-0 ]
  • 38
  • [ 124467-36-3 ]
  • [ 1542133-88-9 ]
  • 39
  • [ 124467-36-3 ]
  • ethyl 5-({2-[2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 40
  • [ 124467-36-3 ]
  • [ 1542134-00-8 ]
  • 41
  • [ 124467-36-3 ]
  • ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 42
  • [ 124467-36-3 ]
  • ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 43
  • [ 124467-36-3 ]
  • [ 1542134-20-2 ]
  • 44
  • [ 124467-36-3 ]
  • rac-ethyl 5-[(2-{5-fluoro-2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)-amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 45
  • [ 124467-36-3 ]
  • (-)-5-{(4-carboxybutyl)[2-(2-[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]-amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid [ No CAS ]
  • 46
  • [ 124467-36-3 ]
  • (+)-ethyl 5-{(tert-butoxycarbonyl)[2-(2-[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)-ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • (-)-ethyl 5-{(tert-butoxycarbonyl)[2-(2-[4-(5-methyl-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)-ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 47
  • [ 124467-36-3 ]
  • [ 1542132-69-3 ]
  • [ 1542132-71-7 ]
  • 48
  • [ 124467-36-3 ]
  • [ 1542133-67-4 ]
  • [ 1542133-65-2 ]
  • 49
  • [ 124467-36-3 ]
  • [ 1542133-90-3 ]
  • [ 1542133-89-0 ]
  • 50
  • [ 124467-36-3 ]
  • [ 1542134-02-0 ]
  • [ 1542134-01-9 ]
  • 51
  • [ 124467-36-3 ]
  • [ 1542133-08-3 ]
  • [ 1542134-09-7 ]
  • 52
  • [ 124467-36-3 ]
  • [ 1542134-10-0 ]
  • [ 1542133-14-1 ]
  • 53
  • [ 124467-36-3 ]
  • [ 1542131-80-5 ]
  • 54
  • [ 124467-36-3 ]
  • [ 1542131-82-7 ]
  • 55
  • [ 124467-36-3 ]
  • [ 1542131-84-9 ]
  • 56
  • [ 124467-36-3 ]
  • [ 1542131-86-1 ]
  • 57
  • [ 124467-36-3 ]
  • [ 1542131-88-3 ]
  • 58
  • [ 124467-36-3 ]
  • [ 1542131-90-7 ]
  • 59
  • [ 124467-36-3 ]
  • [ 1542131-98-5 ]
  • 60
  • [ 124467-36-3 ]
  • [ 1542132-04-6 ]
  • 61
  • [ 124467-36-3 ]
  • [ 1542133-38-9 ]
  • 62
  • [ 124467-36-3 ]
  • ethyl 5-[2-(2-[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}-5-fluorophenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 63
  • [ 124467-36-3 ]
  • ethyl 5-[2-(2-[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}-5-fluorophenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 64
  • [ 124467-36-3 ]
  • ethyl 5-([2-(2-[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}-5-fluorophenyl)ethyl]{2-[4-(methoxycarbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 65
  • [ 124467-36-3 ]
  • ethyl 5-({2-[2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 66
  • [ 124467-36-3 ]
  • ethyl 5-({2-[5-fluoro-2-({4-[2-(4-fluorophenyl)ethyl]benzyl}oxy)phenyl]ethyl}{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate [ No CAS ]
  • 67
  • [ 124467-36-3 ]
  • [ 1542134-16-6 ]
  • 68
  • [ 124467-36-3 ]
  • [ 1542134-18-8 ]
  • 69
  • [ 124467-36-3 ]
  • [ 1542134-19-9 ]
  • 70
  • [ 124467-36-3 ]
  • [ 1542134-22-4 ]
  • 71
  • [ 124467-36-3 ]
  • [ 1542134-23-5 ]
  • 72
  • [ 124467-36-3 ]
  • [ 1542134-68-8 ]
  • 73
  • [ 124467-36-3 ]
  • ethyl 5-[(2-{2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride [ No CAS ]
  • 74
  • [ 124467-36-3 ]
  • [ 33454-16-9 ]
  • 2-chloro-6-(3-(dimethylamino)phenyl)-6-methyl-7,8-dihydroquinolin-5-one [ No CAS ]
  • 75
  • [ 124467-36-3 ]
  • [ 33454-16-9 ]
  • C17H17ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium t-butanolate; In toluene; at 60℃; for 6h;Inert atmosphere; Step-i: Synthesis of 2-chloro-6-(3-chlorophenyl)-7,8-dihydroquinolin-5(6H)-one (26a) To a degased mixture of <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (0.5 g, 0.0027 mol)) and 3- iodo-N,N-dimethylaniline (0.68 g, 0.00276 mol) in toluene (20 mL) was added sodium tert- butoxide (0.53, 0.0055 mol) followed by Pd(Amphos)Cl2 (0.043 g, 0.000055 mol) and stirred under nitrogen for 15 min. The reaction mixture was then heated to 60 C for 6 h. The RM was then cooled to RT, extracted into ethyl acetate, organic portion was dried over sodium sulphate, concentrated to dryness to afford 0.3g of titled compound. This was taken as such into next step without further purification. LC-MS: 301.0 [M+H]+.
  • 76
  • methyl 2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylate [ No CAS ]
  • [ 124467-36-3 ]
  • 77
  • [ 106551-76-2 ]
  • [ 124467-36-3 ]
  • 78
  • [ 124467-36-3 ]
  • 2-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)-7,8-dihydroquinolin-5(6H)-one [ No CAS ]
  • 79
  • [ 13472-85-0 ]
  • [ 124467-36-3 ]
  • 2-chloro-6-(6-methoxypyridin-3-yl)-7,8-dihydroquinolin-5(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium t-butanolate; In toluene; at 20 - 70℃; for 2h;Sealed tube; Inert atmosphere; A mixture of <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (0.4 g, 2.2 mmol), 5-bromo-2-methoxypyridine (0.45 g, 2.4 mmol) and sodium tert-butoxide (0.42 g, 4.4 mmol) in toluene (20mL) was taken in a sealed tube, was degassed with nitrogen gas and added Pd(amphos)C12 (0.0 155 g, 0.02 mmol) at room temperature. Later, the reaction mixture was heated to 70 C for 2 h, cooled it to room temperature, quenched with water and extracted with ethyl acetate. The organic portion was washed with water followed by brine. The separated organic layer was driedover sodium sulphate, filtered and concentrated to get residue which was purified by column chromatography (Silica: 230-400 mesh) using 10% ethyl acetate in hexanes as eluent to afford the title compound (0.2 g, 33%).
  • 80
  • [ 124467-36-3 ]
  • 4-ethyl-2-methyl-6-(phenylsulfonyl)pyrimidine [ No CAS ]
  • 2-chloro-6-(6-ethyl-2-methylpyrimidin-4-yl)-7,8-dihydroquinolin-5(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; for 0.5h;Inert atmosphere; Reflux; To a 50 mL round bottom flask, was added tetrahydrofuran (15 ml). To the same flask, was added 60% sodium hydride in mineral oil (0.88 g, 22.0 mmol), 2-chloro-7,8- dihydroquinolin-5(6H)-one (1.0 g, 5.5 mmol) and 4-ethyl-2-methyl-6- (phenylsulfonyl)pyrimidine (2.89 g, 11.0 mmol) under nitrogen atmosphere. The reaction mixture was refluxed for 30 mm. The reaction mixture was quenched with ice cold water andextracted with dichloromethane. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to get 2-chloro-6-(6-ethyl-2- methylpyrimidin-4-yl)-7, 8-dihydroquinolin-5(6H)-one (1.65 g, crude product). The obtained crude product was used in the next step without further purification. LC-MS: 302.2 [M+H]+.
  • 81
  • [ 124467-36-3 ]
  • 1-(2-methylquinolin-6-ylmethyl)-1H-[1,2,3]triazole-4-carboxylic acid (2-amino-5,6,7,8-tetrahydroquinolin-5-yl)amide [ No CAS ]
  • 82
  • [ 124467-36-3 ]
  • 2-chloro-5,6,7,8-tetrahydroquinolin-5-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
360 mg With methanol; ammonium acetate; sodium cyanoborohydride; at 20℃; for 46h; Step 3: 2-Chloro-5,6,7,8-tetrahydro-quinolin-5-ylamine 2-Chloro-7,8-dihydro-6H-quinolin-5-one (630 mg, 3,40 mmol) and ammonium acetate (2.62 g, 34.0 mmol) are dissolved in methanol (20 ml), then sodium cyanoborohydride (149 mg, 2.38 mmol) is added and the mixture is stirred at room temperature for 48 hours. HCI ( 8 ml 37% aq. solution) is added and methanol is evaporated, the residue is dissolved in water and washed with diethyl ether. Solid KOH is added to the aqueous solution until pH 9 is reached, then the mixture is extracted with diethyl ether. The organic phase is collected, dried over sodium sulphate and concentrated. The residue is purified by flash chromatography (0 - 50% methanol in ethyl acetate) to give the title compound (Yield 360 mg). LC (Method 2): tR = 1 .18 min; Mass spectrum (ES+): m/z = 183 [M+H]+.
  • 83
  • [ 124467-36-3 ]
  • 1-((2-methylquinolin-6-yl)methyl)-1H-[1,2,3]triazole-4-carboxylic acid (2-chloro-5,6,7,8-tetrahydroquinolin-5-yl)amide [ No CAS ]
  • 84
  • [ 124467-36-3 ]
  • 5-oxo-5,6,7,8-tetrahydroquinoline-2-carboxamide [ No CAS ]
  • 85
  • [ 124467-36-3 ]
  • [ 4009-98-7 ]
  • 2-chloro-5,6,7,8-tetrahydroquinoline-5-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% To a stirred suspension of (melhoxymethyi)triphenyiphosphonium chloride (17.0 g, 49.6 mrnol)) in THF (41 mL)was added slowly a solution of potassium 2-methyipropan-2-olate (41 niL, 41 mniol) at 0C via cannula under nitrogen. The resulting cherry-red solution was stirred at 0 C for I h. A solution of 2-chioro- 7.8-dihydroquinoiin-5(6H)-one (3.00 g, 16.5 mmoi) in THF (10.0 mL) was added dropwaise. The reaction mixture was stirred at r.t. for I h. The reaction quenched with water (5 mL). It was concentrated at 35 C to about 40 rnL, then aqueous30% H2S04(15 mL) was added at ri. and it was stirred al 50 C for 16 h. The reaction mixture was gradually poured into saturated sodium carbonate solution (70 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (2x30 mL). The combined organic phases were washed with brine and dried over anhydrous Mg504. After concentration the residue was loaded on a 80gISC() Gold column and eluted with 0 % to 9() % F:tOAc /hexane to provide the title compound (3.0 g. 15.3mmol. 93% yield).
  • 86
  • [ 124467-36-3 ]
  • [ 15258-73-8 ]
  • 2-((2,6-dichlorobenzyl)oxy)-7,8-dihydroquinolin-5(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% A solution of(2,6-dichlorophenyl)methanol (1.07 g, 6.06 mmol) in DMF (15 mL) was treated with NaH (60% in mineral oil; 661 mg, 16.5 mmol) and stirred at rt for 15 mm. The mixture was treated with 2-chloro-7,8-dihydroquinolin-5(6B)-one (1.00 g, 5.51mmol) and stirred at rt for 1.5 h. Chipped ice (5 g) was added and the mixture was extracted twice with EtOAc. The combine organic phases were washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel, eluting with EtOAc-hexanes (0-40%), to provide 2-((2,6-dichlorobenzyl)oxy)-7,8- dihydroquinolin-5(6B)-one (1.35 g, 76% yield). LCMS m/z 321.8, 323.8, 325.8 (M+H), HPLC tR 3.71 mm (method B). 1H NMR (400 MHz, CDCl3) delta 8.21 (d, J=8.58 Hz, 1H), 7.37-7.44 (m, 2H), 7.20-7.33 (m, 1H), 6.71 (d, J=8.58 Hz, 1H), 5.69 (s, 2H), 3.09 (t, J=6.16 Hz, 2H), 2.62-2.70 (m, 2H), 2.14-2.28 (m, 2H).
  • 87
  • [ 124467-36-3 ]
  • [ 402-45-9 ]
  • 2-{4-(trifluoromethyl)phenoxy}-7,8-dihydroquinolin-5(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h; ComuMercially available <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (0.20 g, 1.10 muMol) was dissolved in DMF (5.5mL), and cesium carbonate (0.72 g, 2.20 muMol) and 4-(trifluoromethyl)phenol (0.72 g, 1.65 muMol) were added to thesolution. The mixture was subjected to a reaction at a temperature of 120C for 30 minutes using a microwave reactormanufactured by Biotage. Water was added to the mixture. The organic layer was extracted with ethyl acetate, washedwith saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residuewas purified by silica gel column chromatography (heptane/ethyl acetate = 90/10 -> 60/40) to obtain compound 103-1(0.23 g, 68%).1H NMR (400 MHz, CDCl3, delta): 8.32 (d, J = 8.6 Hz, 1H), 7.68 (d, J = 8.6 Hz, 2H), 7.29 (d, J = 8.6 Hz, 2H), 6.85 (d, J =8.6 Hz, 1H), 2.96 (t, J = 6.1 Hz, 2H), 2.65 (t, J = 6.6 Hz, 2H), 2.15 (tt, J = 6.6, 6.1 Hz, 2H).ESIMS m/z: [M + H]+ 308.
  • 88
  • [ 124467-36-3 ]
  • [ 107-21-1 ]
  • 2'-chloro-7',8'-dihydro-6'H-spiro[[1,3]dioxolane-2,5'-quinoline] [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With pyridinium p-toluenesulfonate; triethylamine; In toluene; for 3h;Dean-Stark; Reflux; ComuMercially available <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (1.50 g, 8.26 muMol) was dissolved in toluene(83 mL). ethylene glycol (0.92 mL, 16.5 muMol) and pyridinium p-toluenesulfonate (208 mg, 0.826 muMol) were added tothe solution,. The mixture was refluxed for three hours using a Dean-Stark apparatus during which ethylene glycol (0.92mL, 16.5 muMol) was added four times every 30 minutes. The mixture was cooled to 0C, and triethylamine (0.35 mL)was added to the mixture. The mixture was concentrated under reduced pressure. The residue was purified by aminosilicagel column chromatography (heptane/ethyl acetate = 90/10 -> 70/30) to obtain compound 35-1 (1.75 g, 94%).1H NMR (400 MHz, CDCl3, delta): 7.73 (d, J = 8.2 Hz, 1H), 7.17 (d, J = 8.2 Hz, 1H), 4.21-4.08 (m, 4H), 2.93 (t, J = 6.1 Hz,2H), 2.03-1.93 (m, 4H); ESIMS m/z: [M + H]+ 226.
  • 89
  • [ 124467-36-3 ]
  • 2'-chloro-7',8'-dihydro-6'H-spiro[[1,3]dioxolane-2,5'-quinolin]-8'-ol [ No CAS ]
  • 90
  • [ 124467-36-3 ]
  • 5-((tert-butyldiphenylsilyl)oxy)-5,6,7,8-tetrahydroquinoline-2-carbonitrile [ No CAS ]
  • 91
  • [ 124467-36-3 ]
  • 1-(5-((tert-butyldiphenylsilyl)oxy)-5,6,7,8-tetrahydroquinoline-2-yl)cyclopropanamine [ No CAS ]
  • 92
  • [ 124467-36-3 ]
  • N-(1-(5-((tert-butyldiphenylsilyl)oxy)-5,6,7,8-tetrahydroquinoline-2-yl)cyclopropyl)-4-fluorobenzamide [ No CAS ]
  • 93
  • [ 124467-36-3 ]
  • 4-fluoro-N-(1-(5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)cyclopropyl)benzamide [ No CAS ]
  • 94
  • [ 124467-36-3 ]
  • N-(1-(5-(3-chlorophenoxy)-5,6,7,8-tetrahydroquinolin-2-yl)cyclopropyl)-4-fluorobenzamide [ No CAS ]
  • 95
  • [ 124467-36-3 ]
  • 4-fluoro-N-(1-(5-hydroxy-5,6,7,8-tetrahydroquinolin-2-yl)cyclopropyl)benzamide [ No CAS ]
  • 96
  • [ 124467-36-3 ]
  • (R)-N-(1-(5-(3-chlorophenoxy)-5,6,7,8-tetrahydroquinolin-2-yl)cyclopropyl)-4-fluorobenzamide [ No CAS ]
  • (S)-N-(1-(5-(3-chlorophenoxy)-5,6,7,8-tetrahydroquinolin-2-yl)cyclopropyl)-4-fluorobenzamide [ No CAS ]
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