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[ CAS No. 238756-47-3 ] {[proInfo.proName]}

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Chemical Structure| 238756-47-3
Chemical Structure| 238756-47-3
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Product Details of [ 238756-47-3 ]

CAS No. :238756-47-3 MDL No. :MFCD11847785
Formula : C9H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :JNHREQJNIDQTRH-UHFFFAOYSA-N
M.W : 178.62 Pubchem ID :15445054
Synonyms :

Calculated chemistry of [ 238756-47-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.16
TPSA : 38.91 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.84
Solubility : 0.256 mg/ml ; 0.00144 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.599 mg/ml ; 0.00335 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.96
Solubility : 0.0198 mg/ml ; 0.000111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 238756-47-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 238756-47-3 ]

* 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 [ 238756-47-3 ]

[ 238756-47-3 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 29969-57-1 ]
  • [ 238756-47-3 ]
YieldReaction ConditionsOperation in experiment
95% With iron; ammonium chloride; In ethanol; water; at 60℃; for 2h; Step 5 2-Chloroquinolin-6-amine: To <strong>[29969-57-1]2-chloro-6-nitroquinoline</strong> (8.4 g, 39.6 mmol) and NH4Cl (6.5 g, 121.50 mmol) was added EtOH (100 mL) and water (20 mL). The reaction mixture was heated to 60 C. and Fe (10 g, 178.6 mmol) was added in several portions. The reaction mixture was stirred for 2 h maintaining the temperature at 60 C. The mixture was cooled to room temperature and the ethanol was removed under reduced pressure. The aqueous mixture was diluted with 100 mL of EtOAc and solids were removed by filtration. The filtrate was concentrated under reduced pressure to yield the desired product, 6.8 g (95%), as a yellow solid.
70% c) 2-Chloroquinoline-6-amine; SnCI2 2 H2O (42 g, 0.19 mol) was added to a stirred solution of <strong>[29969-57-1]2-chloro-6-nitroquinoline</strong> (8.1 g, 39 mmol) in EtOH (250 mL). The mixture was refluxed for 0.5 h, cooled to rt., concentrated and dissolved in DCM (200 mL), added NaOH (150 mL, aq. , 5 M) filtered and rinsed with H20 (150 mL) followed by Et20 (100 mL). The organic phase was washed with NaHC03 (100 mL, aq. , sat. ) and concentrated, which afforded the title compound (4.9 g, 70%) as an orange-yellow, solid material, used in next step without further purification. 'H NMR (300.1 MHz, DMSO-d6) 6 8.01 (d, 1H), 7.62 (d, 1H), 7.30 (d, 1H), 7.19 (dd, 1H), 6.83 (d, 1H), 5.73 (s, 2H). LC-MS [M+H] + 179
  • 2
  • [ 238756-47-3 ]
  • 6,6'-Diamino-2,2'-biquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triphenylphosphine; nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 4h;
  • 3
  • [ 238756-47-3 ]
  • [ 74-88-4 ]
  • C10H9ClN2 [ No CAS ]
  • [ 238756-48-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; for 5.5h; d d) 2-Chloro-N, N-dimethylquinolin-6-amine; MeI (2.8 g, 20 mmol) was added to a stirred solution of 2-chloroquinoline-6-amine (4.7 g, 25 mmol) and K2C03 (3.6 g, 26 mmol) in DMF (300 mL) under nitrogen atmosphere. The mixture was heated to 70 °C for 0.5 h and additional MeI (0.9 g, 6 mmol) was then added, and then stirred for 5 h. The mixture was allowed to reach rt. and poured into H20 (200 mL) and extracted with DCM (2 x 200 mL) and concentrated. Purification of the residue by flash chromatography [120 g silica gel, 6 x 9 cm column, with EtOAc/heptane (2: 3 o 3: 2) followed by DCM: MeOH (95: 5 + 1% Et3N) as eluent] afforded a mixture of mono-and di-N- methylated compounds (0.9 g) as an yellow solid material. The unreacted 2-chloroquinoline- 6-amine isolated (2.8 g) was reacted again in the same manner as described above (1.7 g + 0.7 g MeI, 2.3 g K2CO3, 175 mL DMF) to give an additional 1.7 g of product mixture. The combined batches were purified by flash chromatography (Si02, Heptane: EtOAc) to yield 0.91 g of the title compound. 'H NMR (300.1 MHz, DMSO-d6) 6 8.15 (d, 1H), 7.75 (d, 1H), 7.48 (dd, 1 H), 7.38 (d, 1H), 6.99 (d, 1H), 3.04 (s, 3H), 3.02 (s, 3H). LC-MS [M+H] + 207
  • 4
  • [ 238756-47-3 ]
  • [ 205055-71-6 ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 6-Amino-2-chloroquinoline With hydrogenchloride; acetic acid; sodium nitrite In water; acetonitrile at 0℃; for 0.333333h; Stage #2: With sulfur dioxide In water; acetonitrile at 0℃; for 2h; Stage #3: With copper dichloride In water; acetonitrile at 0 - 20℃; 19.6 Step 6 2-Chloroquinoline-6-sulfonyl chloride: To a solution of 2-chloroquinolin-6-amine (1.0 g, 5.1 mmol) in acetonitrile (50 mL) at 0° C. was added acetic acid (3.3 g, 54.9 mmol) dropwise with stirring over 5 min. To the 0° C. solution was added conc HCl (2 g, 20.3 mmol) dropwise with stirring over 5 min followed by a solution of sodium nitrite (400 mg, 5.7 mmol) in water (1 mL), dropwise with stirring over 10 min. To the cold mixture was introduced sulfur dioxide (0.5 kg, 7.8 mol), while maintaining a temperature of 0° C. over 2 h. To the reaction mixture was added copper(II) chloride dihydrate (900 mg, 5.2 mmol) over 15 min while maintaining a temperature of 0° C. The reaction solution was kept at 0° C. for 50 min and warmed to room temperature overnight. The reaction mixture was then quenched with the addition of 200 mL of H2O/ice. The resulting solution was extracted from CH2Cl2 (3×200 mL). The combined organic layers were washed with water water (3×200 mL), dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography (1:5 EtOAc/hexanes) to afford the desired compound, 0.6 g (43%), as a yellow solid.
  • 5
  • C9H5ClN2O3 [ No CAS ]
  • [ 238756-47-3 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: C9H5ClN2O3 With hydrogenchloride; tin(ll) chloride In water for 1h; Heating; Stage #2: With ammonia In water
  • 6
  • [ 13675-92-8 ]
  • [ 238756-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate 2: hydrogenchloride; tin(ll) chloride / water / 1 h / Heating
  • 7
  • [ 238756-47-3 ]
  • [ 50-00-0 ]
  • [ 238756-48-4 ]
YieldReaction ConditionsOperation in experiment
99% With 2-picoline borane complex; acetic acid In methanol; water at 20℃; for 16h; 1 Synthesis of 359 Synthesis of 359 To a mixture of 358 (2.20 g, 12.3 mmol), an aqueous 36% formaldehyde solution (20.5 g, 246 mmol) and methanol (250 ml)-acetic acid (20 ml), a picoline borane complex (7.91 g, 73.95 mmol) was added little by little, followed by stirring at room temperature for 16 hours. To the reaction solution, ethyl acetate-water was added and the solution was extracted with ethyl acetate after adjusting the pH to 8 using an aqueous potassium carbonate solution. The extraction liquid was washed with water and dried the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane = 1/4) to obtain 359 (2.54 g, 99%) as a pale yellow solid. mp 74-75°C APCI-MS m/z 207[M+H]+
  • 8
  • [ 238756-47-3 ]
  • [ 75-07-0 ]
  • [ 1374108-82-3 ]
YieldReaction ConditionsOperation in experiment
69% With 2-picoline borane complex; acetic acid In methanol at 20℃; for 3.5h; Cooling with ice; 1 Synthesis of 98 Synthesis of 98 To a mixture of 97 (387 mg, 2.17 mmol), acetoaldehyde (2.39 g, 54.3 mmol) and methanol (10 ml) -acetic acid (1 ml), a picoline borane complex (1.16 g, 10.8 mmol) was added under ice cooling and stirring, and the mixture was stirred at room temperature for 3.5 hours. The solvent of the reaction solution was distilled off under reduced pressure and aqueous 10% hydrochloric acid (5 ml) was added to the residue. After stirring at room temperature for 30 minutes, the solution was made basic by adding potassium carbonate. The reaction solution was extracted with chloroform and the extraction liquid was dried, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel flash column chromatography (eluting solvent: n-hexane/ethyl acetate = 19/1) to obtain 98 (353 mg, 69%) as a yellow oily substance. APCI-MS m/z 235/237[M+H]+
  • 9
  • [ 238756-47-3 ]
  • [ 1374107-41-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; 2-picoline borane complex / methanol / 3.5 h / 20 °C / Cooling with ice 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,2-dimethoxyethane / 12 h / 90 °C / Inert atmosphere
  • 10
  • [ 238756-47-3 ]
  • C9H7(18)FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With Quinuclidine; [2.2.2]cryptande; [18F]fluoride ion, cyclotron produced, NCA In water; dimethyl sulfoxide at 200℃; for 0.5h; Inert atmosphere;
YieldReaction ConditionsOperation in experiment
With iron; ammonium chloride In tetrahydrofuran; methanol; water at 60℃; for 18h; Intermediate L: 2-(4-Fluorophenoxy)quinolin-6-amine General procedure: A solution of Intermediate A (260 mg, 0.915 mmol) in methanol (2.7 mL)/THF (5.4 mL)/water (1.1 mL) was treated with ammonium chloride (294 mg, 5.49 mmol) and iron (306 mg, 5.49 mmol). The reaction mixture was heated at 60 °C for 18 h. After cooling to rt, the mixture was filtered through Dicalite, washing with EtOAc. The filtrate was washed with water, dried (MgS04), and concentrated under reduced pressure to afford the title compound as a beige solid (185 mg, 80 %).LCMS (Method D): 1.62 min, (255.1 , MFT)
  • 12
  • [ 59-31-4 ]
  • [ 238756-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 1 h / 0 - 20 °C 2: trichlorophosphate / 2 h / 100 °C 3: iron(0); ammonia hydrochloride / water monomer; ethanol / 3 h / 70 °C
  • 13
  • [ 238756-47-3 ]
  • 2-chloro-5-iodoquinolin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.6% With Iodine monochloride; glacial acetic acid at 20℃; for 3h; 313.2; 426.2 Step 2: 2-chloro-5-iodoquinolin-6-amine To a solution of 2-chloroquinolin-6-amine (4 g,22.3 mmol)in HOAc (20 mL) was added ICl (4.24 g,33.45 mmol) . The mixture was stirred at 20 for 3 hrs and then sat. Na2CO3 solution was added to PH=8-9, the resulting mixture was extracted with EtOAc (70 mL x 3) . The combined organic phase was washed with brine (60 mL) , dried over Na 2SO 4, filtered and concentrated in vacuum. 5-iodo-2-(trifluoromethyl)quinolin-6-amine (6.7 g, 88.6%) was obtained. [M+H] + =304.9.
88.6% With Iodine monochloride; glacial acetic acid at 20℃; for 3h; 313.2; 426.2 Step 2: 2-chloro-5-iodoquinolin-6-amine To a solution of 2-chloroquinolin-6-amine (4 g,22.3 mmol)in HOAc (20 mL) was added ICl (4.24 g,33.45 mmol) . The mixture was stirred at 20 for 3 hrs and then sat. Na2CO3 solution was added to PH=8-9, the resulting mixture was extracted with EtOAc (70 mL x 3) . The combined organic phase was washed with brine (60 mL) , dried over Na 2SO 4, filtered and concentrated in vacuum. 5-iodo-2-(trifluoromethyl)quinolin-6-amine (6.7 g, 88.6%) was obtained. [M+H] + =304.9.
  • 14
  • [ 238756-47-3 ]
  • (6-amino-2-chloroquinolin-5-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere
  • 15
  • [ 238756-47-3 ]
  • (6-amino-2-(prop-1-en-2-yl)quinolin-5-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate / water monomer; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
  • 16
  • [ 238756-47-3 ]
  • (6-amino-2-isopropylquinolin-5-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate / water monomer; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / methanol
  • 17
  • [ 238756-47-3 ]
  • (6-amino-2-cyclopropylquinolin-5-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate / water monomer; 1,4-dioxane / 100 °C
  • 18
  • [ 238756-47-3 ]
  • N-(6-amino-5-(dimethylphosphoryl)quinolin-2-yl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere
  • 19
  • [ 238756-47-3 ]
  • N-(6-((5-bromo-2-chloropyrimidin-4-yl)amino)-5-(dimethylphosphoryl)quinolin-2-yl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / isopropanol / 100 °C
  • 20
  • [ 238756-47-3 ]
  • N-(6-((5-bromo-2-((5-ethyl-2-methoxy-4-(4-(piperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)-5-(dimethylphosphoryl)quinolin-2-yl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / isopropanol / 100 °C 5: toluene-4-sulfonic acid / butan-1-ol / 16 h / 100 °C
  • 21
  • [ 238756-47-3 ]
  • N-(6-((5-bromo-2-((4-(4-(4-((R)-1-(4-((R)-2,6-dioxopiperidin-3-yl)-3,5-difluorophenyl)pyrrolidine-3-carbonyl)piperazin-1-yl)piperidin-1-yl)-5-ethyl-2-methoxyphenyl)amino)pyrimidin-4-yl)amino)-5-(dimethylphosphoryl)quinolin-2-yl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: glacial acetic acid; Iodine monochloride / 3 h / 20 °C 2: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Cs2CO3 / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / isopropanol / 100 °C 5: toluene-4-sulfonic acid / butan-1-ol / 16 h / 100 °C 6: N-ethyl-N,N-diisopropylamine; 1-propanephosphonic acid cyclic anhydride / dichloromethane / 1 h / 20 °C
  • 22
  • [ 64495-55-2 ]
  • [ 238756-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate / 2 h / 100 °C 2: iron(0); ammonia hydrochloride / water monomer; ethanol / 3 h / 70 °C
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