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[ CAS No. 71569-15-8 ] {[proInfo.proName]}

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Chemical Structure| 71569-15-8
Chemical Structure| 71569-15-8
Structure of 71569-15-8 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 71569-15-8 ]

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Product Details of [ 71569-15-8 ]

CAS No. :71569-15-8 MDL No. :MFCD04038438
Formula : C9H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZMAFTVCNAYZLGF-UHFFFAOYSA-N
M.W : 148.20 Pubchem ID :156182
Synonyms :

Calculated chemistry of [ 71569-15-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.38
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 0.53
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 1.7
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.5
Solubility : 4.73 mg/ml ; 0.0319 mol/l
Class : Very soluble
Log S (Ali) : -0.92
Solubility : 17.9 mg/ml ; 0.121 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.443 mg/ml ; 0.00299 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.36

Safety of [ 71569-15-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 71569-15-8 ]

* 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 [ 71569-15-8 ]

[ 71569-15-8 ] Synthesis Path-Downstream   1~16

  • 2
  • [ 71569-15-8 ]
  • [ 75-36-5 ]
  • [ 185510-52-5 ]
  • 4
  • [ 71569-15-8 ]
  • [ 141-78-6 ]
  • (S)-5,6,7,8-tetrahydroquinolin-5-ylamine [ No CAS ]
  • (R)-N-(5,6,7,8-tetrahydroquinolin-5-yl)acetamide [ No CAS ]
  • 5
  • [ 71569-15-8 ]
  • Ethyl-methyl-(5,6,7,8-tetrahydro-quinolin-5-yl)-amine; hydrochloride [ No CAS ]
  • 6
  • [ 71569-15-8 ]
  • Ethyl-(5,6,7,8-tetrahydro-quinolin-5-yl)-amine; compound with (Z)-but-2-enedioic acid [ No CAS ]
  • 7
  • [ 71569-15-8 ]
  • [ 185510-56-9 ]
  • 8
  • [ 71569-15-8 ]
  • [ 185510-03-6 ]
  • 9
  • [ 185510-52-5 ]
  • [ 298182-09-9 ]
  • [ 71569-15-8 ]
  • [ 133091-81-3 ]
YieldReaction ConditionsOperation in experiment
48%; 43% With hydrogenchloride; In methanol; water; for 48.0h;Heating / reflux; To a vigorously stirred solution of 5-(N-acetylamino)-quinoline and 7-(N-acetylamino)-quinoline (2.7 g, 14 mmol) in TFA (30 mL) in a 250 mL round-bottom flask under nitrogen was added PtO2 (165 mg, 0.72 mmol). The flask was then flushed with H2 for 5 min, then placed under a H2 atmosphere (H2 balloon) and heated to 60 C. for 18 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated. The residue was rendered basic with a minimum volume of 4 N NaOH and extracted with CHCl3 (3×50 mL), and the combined extracts were dried (MgSO4) and concentrated in vacuo. Purification of the residue by column chromatography on silica gel (CHCl3/MeOH/NH4OH 20:2:1) afforded 1.35 g of a mixture of 5-(N-acetylamino)-5,6,7,8-tetrahydroquinoline and 7-(N-acetylamino)-5,6,7,8-tetrahydroquinoline, respectively (49% yield). The mixture (1.35 g, 7.1 mmol) was dissolved in MeOH (20 mL) and concentrated HCl (5 mL) was added; the solution was then heated at reflux for 2 days. The reaction was then cooled to room temperature and the volume was reduced by evaporation. The residue was (cautiously) made basic with a minimum amount of saturated aqueous NaOH, then the aqueous phase was extracted with CHCl3 (3×25 mL), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification of the residue by radial chromatography on silica gel (4 mm plate, CHCl3/MeOH/NH4OH 20:2:1) afforded two products: 7-amino-5,6,7,8-tetrahydroquinoline (AMD8850) (456 mg, 43%) as a pale yellow oil. 1H NMR (CDCl3) delta 1.45 (br s, 2H), 1.48-1.54 (m, 1H), 1.88-1.90 (m, 1H), 2.59 (dd, 1H, J=15, 9 Hz), 2.71-2.78 (m, 2H), 3.08 (dd, 1H, J=15, 6 Hz), 3.18-3.24 (m, 1H), 6.93 (dd, 1H, J=8, 5 Hz), 7.27 (br d, 1H, J=8 Hz), 8.25 (br d, 1H, J=5 Hz); 13C NMR (CDCl3) delta 26.4, 31.8, 42.1, 46.8, 120.8, 130.8, 136.1, 146.8, 155.4; ES-MS m/z 149 (M+H); and 5-amino-5,6,7,8-tetrahydroquinoline (AMD8851) (503 mg 48%) as a pale yellow oil. 1H NMR (CDCl3) delta 1.57-1.65 (m, 3H), 1.78-1.81 (m, 1H), 1.93-2.00 (m, 2H), 2.79-2.89 (m, 2H), 3.90-3.92 (m, 1H), 7.04 (dd, 1H, J=8, 5 Hz), 7.67 (br d, 1H, J=8 Hz), 8.32 (br d, 1H, J=5 Hz); 13C NMR (CDCl3) delta 19.2, 29.5, 32.3, 33.4, 49.1, 121.2, 135.7, 136.0, 147.5, 156.7. ES-MS m/z 149 (M+H).
  • 10
  • [ 1119718-08-9 ]
  • [ 71569-15-8 ]
  • [ 1123149-24-5 ]
YieldReaction ConditionsOperation in experiment
54% In methylsulphoxide; at 90.0℃; for 72.0h; In a 25 mL round bottom flask was placed 4-(6-fluoro-5-methylpyridin-3-yl)-6,7-dimethoxycinnoline (0.1070 g, 0.36 mmol) and <strong>[71569-15-8]5,6,7,8-tetrahydroquinolin-5-amine</strong> (0.5301 g, 3.6 mmol) in methylsulfoxide at 90 C. to stir for 72 hours. The reaction was monitored by LCMS and was cooled when 80% of starting material was consumed. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, saturated sodium chloride solution, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40 M), eluting with a gradient of 1% to 5% methanol in dichloromethane, to provide N-(5-(6,7-dimethoxycinnolin-4-yl)-3-methylpyridin-2-yl)-<strong>[71569-15-8]5,6,7,8-tetrahydroquinolin-5-amine</strong> (0.0831 g, 54% yield, M+1=428.2).
  • 11
  • [ 1943-83-5 ]
  • [ 71569-15-8 ]
  • C12H16ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20.0℃; for 1.5h; To 5,6,7,8-tetrahydroquinolin-8-amine (Intermediate 17) (3.0 mmol) in dichloromethane (10 mL) was added chloroethylisocyanate (3.3 mmol). The solution was stirred at room temperature for 1.5 hour. The solvent was removed under vacuum gave a crude material, which was refluxed in H2O (60 mL) for 1 hour. After cooling to room temperature, the reaction was basified with NaOH (pH 14), extracted in Ethyl acetate (3 x 50 mL). The pooled organic layers were washed with brine and dried over magnesium sulphate to give 747. (4, 5-Dihydro-oxazol-2-yl)-(5,6,7,8-tetrahydro- quinolin-8-yl)-amine, 747 as a solid.1HNMR (CDCl3, 300MHz): delta = 6.89-7.34 (m, 4H), 5.21 (s, J= 4.5 Hz, IH), 4.01- 4.07 (m, 2H), 3.34-3.39 (m, 2H), 2.82-2.96 (m, 2H), 2.59-2.67 (m, IH), 1.91-1.99 (m, IH).
  • 12
  • [ 1114896-36-4 ]
  • [ 71569-15-8 ]
YieldReaction ConditionsOperation in experiment
78% With hydrogen;palladium 10% on activated carbon; In methanol; under 2585.81 Torr; for 16.0h; A mixture of Z/E)-7,8-dihydroquinolin-5(6H)-one O-methyl oxime, (Intermediate 23) (1.14 g, 6.47 mmol) in TFA (20 Ml) was added 10% palladium on carbon (10 wt% of Pd/C; 0.15 g) under argon in a Parr shaker flask. The mixture was <n="14"/>hydrogenated at 50 psi for 16 hours. The reaction mixture was flushed with nitrogen and filtered through a plug of Celite and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel using NH3-MeOHiCH2Cl2 to afford, 5,6,7,8-tetrahydroquinolin-5-amine, (Intermediate 22), (0.74 g, 78%). 1HNMR (CD3OD, 300MHz): delta = 8.41 (d, J= 4.5 Hz, 1 H), 7.43 (d, J= 8.1 Hz, 1 H), 7.15-7.11 (m, IH), 4.18 (m, IH), 2.85-2.80, (m, 2 H), 2.35-2.29 (m, 1 H), 2.05-2.01 (m, 1 H), 1.99-1.77 (m, 2H).
  • 13
  • [ 71569-15-8 ]
  • tert-butyl N-methyl-N-(5,6,7,8-tetrahydroquinolin-5-yl)carbamate [ No CAS ]
  • 14
  • [ 71569-15-8 ]
  • N-methyl-5,6,7,8-tetrahydroquinolin-5-amine dihydrochloride [ No CAS ]
  • 15
  • [ 24424-99-5 ]
  • [ 71569-15-8 ]
  • tert-butyl N-(5,6,7,8-tetrahydroquinolin-5-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20.0℃; for 1.0h; To a 20 mL vial was added 5,6,7,8-tetrahy roquinolin-5-amine (500 mg, 3.4 mmol) followed by tert-butoxycarbonyl tert-butyl carbonate (773 mg , 3.5 mmol), 6 mL of tetrahydrofuran, and 6 mL of saturated sodium bicarbonate. The reaction was shaken at room temperature for lh. LCMS showed product formation. The reaction was diluted with ethyl acetate, and washed with water. Organic phase was then concentrated under reduced pressure, The crude product was carried on directly without purification. LCMS M/Z (M+H) 249.
  • 16
  • [ 71569-15-8 ]
  • [ 1114896-34-2 ]
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