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[ CAS No. 78060-54-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 78060-54-5
Chemical Structure| 78060-54-5
Chemical Structure| 78060-54-5
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Product Details of [ 78060-54-5 ]

CAS No. :78060-54-5 MDL No. :MFCD09038087
Formula : C10H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :FQQBAJVDVDHSSF-UHFFFAOYSA-N
M.W : 188.61 Pubchem ID :11252468
Synonyms :

Calculated chemistry of [ 78060-54-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.47
TPSA : 36.68 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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 1.7
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.147 mg/ml ; 0.000777 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.271 mg/ml ; 0.00144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.4
Solubility : 0.00744 mg/ml ; 0.0000394 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 78060-54-5 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 78060-54-5 ]

* 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 [ 78060-54-5 ]

[ 78060-54-5 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 63124-11-8 ]
  • [ 78060-54-5 ]
YieldReaction ConditionsOperation in experiment
80% With trichlorophosphate at 110℃; for 2h;
14 g With trichlorophosphate at 120℃; for 16h; 1.A2 Step A-2: Preparation of 2-chloroquinoline-6-carbonitrile A suspension of 2-oxo-1 H-quinoline-6-carbonitrile (15.0 g, 88.0 mmol) in POC (130 mL) was heated at 120° C for 16 h. The reaction mixture was cooled to room temperature, poured on to crushed ice, resulted solids filtered and dried under vacuum to afford 2-chloroquinoline-6-carbonitrile (14.0 g) as brown solid. (0522) NMR (300 MHz, DMSO-c/e): δ 8.73 (s, 1 H), 8.57 (d, 1 H), 8.09-8.16 (m, 2H), 7.78 (d, 1 H). (0523) MS (method D) m/z: 189.1 [M + H]+
  • 2
  • [ 20327-23-5 ]
  • [ 78060-54-5 ]
  • [ 577967-93-2 ]
  • 4
  • [ 327058-51-5 ]
  • [ 78060-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1.5 h / 20 °C 2.1: 1-methyl-pyrrolidin-2-one / 7 h / 202 °C 2.2: 91 percent / FeCl3*6H2O; aq. HCl / 72 h / 20 °C 3.1: 80 percent / POCl3 / 2 h / 110 °C
  • 5
  • [ 78060-54-5 ]
  • cyclopropyl-[2-(4-cyclopropyl-piperazin-1-yl)-quinolin-6-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: various solvent(s) / 44 h / 95 °C 2.1: Mg / tetrahydrofuran / 20 °C 2.2: tetrahydrofuran / 5 h / 20 °C
  • 6
  • [ 78060-54-5 ]
  • [2-(4-cyclopropyl-piperazin-1-yl)-quinolin-6-yl]-(4-fluoro-phenyl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: various solvent(s) / 44 h / 95 °C 2: tetrahydrofuran; diethyl ether / 20 °C
  • 8
  • [ 7755-92-2 ]
  • [ 78060-54-5 ]
  • 2-(piperazin-1-yl)quinoline-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: piperazine-1-carbaldehyde; 2-chloroquinoline-6-carbonitrile In N,N-dimethyl-formamide at 130℃; for 4h; Inert atmosphere; Stage #2: With sulfuric acid In water; N,N-dimethyl-formamide at 130℃; for 9h; Inert atmosphere;
  • 10
  • [ 1810-71-5 ]
  • copper(l) cyanide [ No CAS ]
  • [ 78060-54-5 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 150℃; 2.A Step A: 2-chloroquinoline-6-carbonitrile Step A: 2-chloroquinoline-6-carbonitrile: To a flask containing a stir bar was added 6-bromo-2- chloroquinoline (0.90 g, 3.7 mmol), CuCN (0.50 g, 5.6 mmol) followed by addition of DMF (10 mL). The resulting mixture was then refluxed at 150 °C overnight. When the reaction appeared complete by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered, redissolved in DCM, absorbed onto silica gel, and purified by flash chromatography to provide the title product.
  • 11
  • [ 78060-54-5 ]
  • [ 1431869-45-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C / Inert atmosphere 2: trifluoroacetic acid / 0.33 h 3: ethanol / 1 h / 140 °C
  • 12
  • [ 78060-54-5 ]
  • [ 1431869-09-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C / Inert atmosphere 2: trifluoroacetic acid / 0.33 h
  • 13
  • [ 76003-29-7 ]
  • [ 78060-54-5 ]
  • [ 1431869-10-1 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Inert atmosphere; 2.B Step B: tert-Butyl 4-(6-cvanoquinolin-2-yl')-3-oxopiperazine-l-carboxylate: Step B: tert-Butyl 4-(6-cvanoquinolin-2-yl')-3-oxopiperazine-l-carboxylate:To a 25 mL flask was added a stir bar, 2-chloroquinoline-6-carbonitrile (0.015 g, 0.79 mmol), Pd2dba3 (0.072 g, 0.08 mmol), Xantphos (0.09 g, 0.16 mmol), cesium carbonate (0.36 g, 1.13 mmol) and tert-Butyl 3-oxopiperazine-l-carboxylate (0.31 g, 1.6 mmol). The resulting mixture was degassed and purged with N2 (3X). To the flask was added 1,4-dioxane (10 mL). The reaction mixture was then refluxed at 100 °C overnight. Analysis of the reaction mixture by LC indicated that reaction had gone to completion. The solution was concentrated in vacuo and the resulting crude was dissolved in EtOAc and washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (10% MeOH in DCM) to provide the title product.
  • 14
  • C13H14F3NO [ No CAS ]
  • [ 78060-54-5 ]
  • C23H18F3N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.8% With potassium carbonate In acetonitrile for 16h; Reflux; Preparation of intermediate AY Preparation of intermediate AY A mixture of 2-chloro-6-quinolinecarbonitrile (CAS [78060-54-5], 14.7 mg, 0.078 mmol), Intermediate T (20.0 mg, 0.078 mmol) and potassium carbonate (21.6 mg, 0.156 mmol) in acetonitrile (5 mL) was refluxed for 16 hours. The solvent was evaporated under vacuum. The residue was purified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate 1/1) to give intermediate AY (20.0 mg, yield: 62.8%).
  • 15
  • [ 78060-54-5 ]
  • tert-butyl N-(6-carbamoyl-2-quinolyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h
  • 16
  • [ 78060-54-5 ]
  • tert-butyl N-[6-[(E)-dimethylaminomethylenecarbamoyl]-2-quinolyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3: N,N-dimethyl acetamide / 4 h / 90 °C
  • 17
  • [ 78060-54-5 ]
  • tert-butyl N-[6-(1H-1,2,4-triazol-3-yl)-2-quinolyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3: N,N-dimethyl acetamide / 4 h / 90 °C 4: acetic acid; hydrazine hydrate / 1 h / 80 °C
  • 18
  • [ 78060-54-5 ]
  • 6-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]quinolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3: N,N-dimethyl acetamide / 4 h / 90 °C 4: acetic acid; hydrazine hydrate / 1 h / 80 °C 5: caesium carbonate; 8-quinolinol; copper(l) iodide / N,N-dimethyl-formamide; water / 16 h / 150 °C
  • 19
  • [ 78060-54-5 ]
  • 1-(2-isopropylphenyl)-3-[6-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-2-quinolyl]thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2.1: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3.1: N,N-dimethyl acetamide / 4 h / 90 °C 4.1: acetic acid; hydrazine hydrate / 1 h / 80 °C 5.1: caesium carbonate; 8-quinolinol; copper(l) iodide / N,N-dimethyl-formamide; water / 16 h / 150 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 6.2: 16 h / 0 - 60 °C
  • 20
  • [ 78060-54-5 ]
  • 1-(2-isopropylphenyl)-3-[6-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-2-quinolyl]urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3: N,N-dimethyl acetamide / 4 h / 90 °C 4: acetic acid; hydrazine hydrate / 1 h / 80 °C 5: caesium carbonate; 8-quinolinol; copper(l) iodide / N,N-dimethyl-formamide; water / 16 h / 150 °C 6: potassium carbonate / acetonitrile / 16 h / 20 °C
  • 21
  • [ 78060-54-5 ]
  • 3-(2-isopropylphenyl)-N-[6-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-2-quinolyl]-1,3-thiazetidin-2-imine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2.1: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3.1: N,N-dimethyl acetamide / 4 h / 90 °C 4.1: acetic acid; hydrazine hydrate / 1 h / 80 °C 5.1: caesium carbonate; 8-quinolinol; copper(l) iodide / N,N-dimethyl-formamide; water / 16 h / 150 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 6.2: 16 h / 0 - 60 °C 7.1: potassium carbonate / butanone / 55 °C
  • 22
  • [ 78060-54-5 ]
  • N-(3-(2-isopropylphenyl)-4-methylthiazol-2(3H)-ylidene)-6-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)quinolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2.1: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3.1: N,N-dimethyl acetamide / 4 h / 90 °C 4.1: acetic acid; hydrazine hydrate / 1 h / 80 °C 5.1: caesium carbonate; 8-quinolinol; copper(l) iodide / N,N-dimethyl-formamide; water / 16 h / 150 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 6.2: 16 h / 0 - 60 °C 7.1: triethylamine / butanone / 24 h / 20 °C
  • 23
  • [ 78060-54-5 ]
  • (2Z)-3-(2-isopropylphenyl)-2-[[6-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-2-quinolyl]imino]thiazolidin-4-one [ No CAS ]
  • (2E)-3-(2-isopropylphenyl)-2-[[6-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]-2-quinolyl]imino]thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2.1: potassium carbonate; dihydrogen peroxide / dimethylsulfoxide-d6 / 2.17 h 3.1: N,N-dimethyl acetamide / 4 h / 90 °C 4.1: acetic acid; hydrazine hydrate / 1 h / 80 °C 5.1: caesium carbonate; 8-quinolinol; copper(l) iodide / N,N-dimethyl-formamide; water / 16 h / 150 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 6.2: 16 h / 0 - 60 °C 7.1: triethylamine / butanone / 6 h / 60 °C
  • 24
  • [ 4248-19-5 ]
  • [ 78060-54-5 ]
  • tert-butyl N-(6-cyano-2-quinolyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
10 g With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium hydroxide In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 1.A3 Step A-3: Preparation of tert-butyl N-(6-cyano-2-quinolyl)carbamate A suspension of 2-chloroquinoline-6-carbonitrile (14.0 g, 75.0 mmol) in 1 , 4 dioxane (230 mL) was charged with tert-butyl carbamate (9.60 g, 82.0 mmol) and NaOH (4.46 g, 1 16 mmol) at room temperature followed by degassing with argon for 10 min. Pd(OAc)2 (0.50 g, 0.75 mmol) and (0526) Xanthphos (0.86 g, 1 .48 mmol) were added to the reaction mixture and heated at 100 °C for 16 h. The reaction mixture was cooled to room temperature, filtered through celite bed, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to afford tert-butyl N-(6-cyano-2-quinolyl)carbamate (10.0 g) as an off white solid. (0527) H NMR (300 MHz, CDCIs): δ 8.26 (d, 1 H), 8.13-8.18 (m, 2H), 8.04 (s, 1 H), 7.84 (d, 1 H), 7.78 (d, 1 H), (0528) 7.75 (d, 1 H), 1.51 (s, 9H). (0529) MS (method D) m/z: 270.1 [M + H]+
  • 25
  • N-(5-(((2S,4R)-4-hydroxy-2-methylpyrrolidin-1-yl)methyl)thiazol-2-yl)acetamide [ No CAS ]
  • [ 78060-54-5 ]
  • 2-(((3R,5S)-1-((2-acetamidothiazol-5-yl)methyl)-5-methylpyrrolidin-3-yl)oxy)quinoline-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(5-(((2S,4R)-4-hydroxy-2-methylpyrrolidin-1-yl)methyl)thiazol-2-yl)acetamide With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; Stage #2: 2-chloroquinoline-6-carbonitrile In dimethyl sulfoxide at 60℃; 2 General Procedure 1 General procedure: tert- butyl (25,4R)-4-hydroxy-2- methyl-pyrrolidine- 1 -carboxylatc (1 equiv.) was dissolved in DMSO (0.5 ml), and /BuOK (1.2 equiv.) was then added and the mixture was stirred at room temperature for 30-40 minutes. The corresponding bicyclic Het-X (1.2 equiv) was added and the mixture was stirred at 60 °C for 16 - 72 hours. The mixture was neutralized by addition of AcOH (1.5 equiv.) and product was purified by C18 prep-HPLC (gradient mixture MeOH/H2O) to afford the desired compound.
  • 26
  • C22H26N4O3 [ No CAS ]
  • [ 78060-54-5 ]
  • C32H30N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 12h; 5 Synthesis of intermediate 5b: Intermediate 1d (3.9g, 10.0mmol), compound 5a (1.9g, 10.0mmol), tris(dibenzylideneacetone) two palladium (Pd2(dba) 3,458mg, 0.5mmol), 4,5-bis Diphenylphosphine-9,9-dimethylxanthene (Xantphos, 578mg, 1.0mmol), Cs2CO3 (4.9g, 15.0mmol) are dissolved in N,N-dimethylformamide (DMF, 50mL), The temperature was raised to 100°C and the reaction was stirred for 12 hours. The reaction was monitored by TLC. After the reaction, the pH was adjusted to 5-6 with dilute hydrochloric acid, and then the reaction solution after the reaction was extracted twice with ethyl acetate. The volume is 50 mL, the organic layers are combined, the organic layers are dried, filtered, and the filtrate is concentrated to obtain a pale yellow oily liquid, which is intermediate 5b, which is directly used in the next reaction without purification.
  • 27
  • C21H25N5O3 [ No CAS ]
  • [ 78060-54-5 ]
  • C31H29N7O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 6h; 17 Synthesis of intermediate 17a: Intermediate 13c (3.9g, 10.0mmol), compound 5a (1.9g, 10.0mmol), tris(dibenzylideneacetone) two palladium (Pd2(dba) 3,458mg, 0.5mmol), 4,5-bis Diphenylphosphine-9,9-dimethylxanthene (Xantphos, 578mg, 1.0mmol), Cs2CO3 (4.9g, 15.0mmol) are dissolved in N,N-dimethylformamide (DMF, 50mL), The temperature was raised to 100°C and the reaction was stirred for 6 hours. The reaction was monitored by TLC. After the reaction, the pH was adjusted to 5-6 with dilute hydrochloric acid, and then the reaction solution after the reaction was extracted twice with ethyl acetate. The volume is 50 mL, the organic layers are combined, the organic layers are dried, filtered, and the filtrate is concentrated to obtain a pale yellow oily liquid, which is Intermediate 17a, which is directly used in the next reaction without purification.
  • 28
  • 2-hydroxyquinoline-6-carbonitrile [ No CAS ]
  • [ 78060-54-5 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 110℃; for 2h; 36.2 2-hydroxyquinoline-6-carbonitrile (1.3 g, 7,64 mmol, 1 eq) in POCl3 (13.20 g, 86.09 mmol, 8 mL, 11.27 eq) was stirred at 110 °C for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was added to H2O 100 mL at 25 °C slowly. Hie mixture was extracted with EtOAc 150 mL (50 mL * 3). The combined organic layers were washed with brine 30 mL, dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. Compound 2-chloroquinoline-6-carbonitrile (400 mg, crude) was obtained as black solid without further purification. LCMS: (M+H)+ : 189.0.
  • 29
  • [ 22246-13-5 ]
  • [ 78060-54-5 ]
  • 2-[(2-oxo-3,4-dihydro-1H-quinolin-6-yl)amino]quinoline-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
19 mg With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 10h; Inert atmosphere; 36.3 To a solution of 2-chloroquinolme-6-carbonitrile (200 mg, 1.06 mmol, 1 eq) and 6-amino-3,4-dihydro-1H-quinolin-2-one (171.98 mg, 1.06 mmol, 1 eq) in dioxane (5 mL) was added Pd(OAc)2 (47.61 mg, 212.07 umol, 0.2 eq), Cs2CO3 (690.98 mg, 2.12 mmol, 2 eq) and Xantphos (122.71 mg, 212.07 umol, 0.2 eq). The mixture was stirred at 80 °C for 10 hr under N2. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Waters Abridge Prep OBD C18 150*40mm*10um;mobile phase: [water(0.05%NH3H2O+10mM NH4HCO3)-ACN];B%: 35%-65%,8min) to give 2-[(2-oxo-3,4-dihydro-1H-quinolin-6- yl)amino]quinoline-6-carbonitrile (88,19 mg, 99% purity), LCMS: (M+H)+ : 315.1, and 2- [[1-(6-cyano-2-quinolyl)-2-oxo-3,4-dihydroquinolin-6-y.]amino]quinoline~6-carbonitrile (20 mg, 98% purity), LCMS: (M+H)+ : 467.2.
  • 30
  • [ 1810-66-8 ]
  • [ 78060-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one / 5 h / 180 °C 2: trichlorophosphate / 2 h / 110 °C
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