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[ CAS No. 298181-83-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 298181-83-6
Chemical Structure| 298181-83-6
Chemical Structure| 298181-83-6
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Product Details of [ 298181-83-6 ]

CAS No. :298181-83-6 MDL No. :MFCD08234982
Formula : C9H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :JQGOUNFVDYUKMM-UHFFFAOYSA-N
M.W : 148.21 Pubchem ID :11355564
Synonyms :

Calculated chemistry of [ 298181-83-6 ]

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) : 1.61
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 : 1.16

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 : 2.32

Safety of [ 298181-83-6 ]

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 [ 298181-83-6 ]

* 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.

  • Upstream synthesis route of [ 298181-83-6 ]
  • Downstream synthetic route of [ 298181-83-6 ]

[ 298181-83-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 58509-59-4 ]
  • [ 298181-83-6 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen In methanol for 18 h; A solution of 6,7-dihydro-8(5H)-quinolinone oxime (0.50 g, 3.1 mmol, Synthetic Communications, 2003, 33, 3497-3502) in 35 ml_ of MeOH was subjected to catalytic hydrogenation at 50 psi in the presence of 50 mg of 10percent Pd on carbon. After 18 hours the reaction vessel was purged with nitrogen, catalyst removed by filtration through celite, and the filtrate concentrated to dryness at reduced pressure to afford 0.42 g (92percent) of 5,6,7,8-tetrahydro-8-quinolinamine as a purple oil. 1H NMR (CDCI3): 5 8.39 (d, 1H), 7.36 (d, 1H), 7.04 (m, 1H), 4.00 (t, 1H), 2.88-2.67 (m, 2H), 2.18 (m, 1H), 2.03-1.62 (m,5H).
Reference: [1] Patent: WO2006/20415, 2006, A1, . Location in patent: Page/Page column 112
[2] Synthetic Communications, 2003, vol. 33, # 20, p. 3497 - 3502
[3] Organic Process Research and Development, 2008, vol. 12, # 5, p. 823 - 830
[4] Chemical Communications, 2016, vol. 52, # 38, p. 6423 - 6426
  • 2
  • [ 1374781-10-8 ]
  • [ 298181-83-6 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With hydrogen In methanol
Stage #2: at 115 - 140℃;
To a solution of the azide (41.0 g, 0.256 mol) in methanol (250 mL) was added Pd/C (10percent, 4.1 g) and the mixture was hydrogenated at 30 psi on a Parr shaker. The mixture was filtered through celite and the cake was washed with methanol. The combined filtrates were evaporated and the residual oil was distilled (Kugelrohr, bp 115-140° C. @ 0.2 Torr) to provide 26.8 g (71percent) of 8-amino-5,6,7,8-tetrahydroquinoline (AMD7488) as a pale yellow oil. 1H NMR (MeOH-d4) δ 1.81-1.98 (m, 2H), 2.03-2.15 (m, 1H), 2.38-2.46 (m, 1H), 2.88-2.92 (m, 2H), 4.41 (dd, 1H, J=9.3, 6.3 Hz), 7.30 (dd, 1H, J=7.5, 4.5 Hz), 7.62 (d, 1H, J=7.5 Hz), 8.47 (d, 1H, J=4.5 Hz); 13C NMR (MeOH-d4) δ 21.12, 28.72, 28.89, 52.28, 124.86, 134.35, 138.96, 148.49, 152.57. ES-MS m/z 149 (M+H).
Reference: [1] Patent: US6750348, 2004, B1, . Location in patent: Page column 16
  • 3
  • [ 56826-69-8 ]
  • [ 298181-83-6 ]
YieldReaction ConditionsOperation in experiment
92% With 10% palladium on activated charcoal; ammonia; hydrogen In methanol at 20℃; for 12 h; Under stirring To a solution of 6,7-dihydroquinoline-8(5H)-one (205 mg, 1.4 mmol) in 5 mL of saturated methanolic ammonia was added palladium on carbon (21 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 12 h. Filtered to remove palladium carbon, The filtrate is concentrated, Column chromatography of the residue gave the title compound as a red oil (189 mg, 92percent yield).
Reference: [1] Patent: CN103570683, 2018, B, . Location in patent: Paragraph 0627; 0628; 0636; 0637
[2] Tetrahedron Letters, 2010, vol. 51, # 39, p. 5210 - 5212
[3] Chemical Communications, 2016, vol. 52, # 38, p. 6423 - 6426
  • 4
  • [ 125163-05-5 ]
  • [ 405174-59-6 ]
  • [ 298181-83-6 ]
Reference: [1] Patent: US2004/19058, 2004, A1,
  • 5
  • [ 369655-84-5 ]
  • [ 298181-83-6 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3546 - 3551
  • 6
  • [ 502612-35-3 ]
  • [ 298181-83-6 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3546 - 3551
  • 7
  • [ 10500-57-9 ]
  • [ 298181-83-6 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 20, p. 3497 - 3502
[2] Organic Process Research and Development, 2008, vol. 12, # 5, p. 823 - 830
  • 8
  • [ 477531-98-9 ]
  • [ 298181-83-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3376 - 3388
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