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[ CAS No. 635-80-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 635-80-3
Chemical Structure| 635-80-3
Chemical Structure| 635-80-3
Structure of 635-80-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 635-80-3 ]

CAS No. :635-80-3 MDL No. :MFCD00748504
Formula : C11H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IZONZQFTYGVOOO-UHFFFAOYSA-N
M.W : 187.20 Pubchem ID :604483
Synonyms :

Calculated chemistry of [ 635-80-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.67
TPSA : 50.19 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.12
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 1.63
Log Po/w (SILICOS-IT) : 2.28
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.298 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.81
Solubility : 0.293 mg/ml ; 0.00157 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.0645 mg/ml ; 0.000344 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 635-80-3 ]

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 [ 635-80-3 ]

* 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.

  • Upstream synthesis route of [ 635-80-3 ]
  • Downstream synthetic route of [ 635-80-3 ]

[ 635-80-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 150-13-0 ]
  • [ 123-73-9 ]
  • [ 635-80-3 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With hydrogenchloride In water for 2 h; Reflux
Stage #2: for 12.75 h;
Intermediate 13: (2-methylquinolin-6-yl)methanamine Stepl : 2-methylquinoline-6-carboxylic acid: To 4-aminobenzoic acid (5 g, 36.45 mmol) , 6N HCl (73 ml) was added and refluxed for 2h. Crotonaldehyde (3.06 g, 43.75 mmol) was added dropwise over 45 min.. After 12h, the reaction mixture was cooled to 0°C and the pH adjusted to 3-5 with aqueous ammonia solution. The aqueous layer containing solid was washed with dichloromethane and acidified with 2N HCl, filtered and dried under vacuum to afford the title compound as brown solid (3.0 g, 44percent).
44%
Stage #1: With hydrogenchloride In water for 2 h; Reflux
Stage #2: for 12 h;
Step 1:
2-methylquinoline-6-carboxylic acid
To 4-aminobenzoic acid (5 g, 36.45 mmol), 6N HCl (73 ml) was added and refluxed for 2 h.
Crotonaldehyde (3.06 g, 43.75 mmol) was added dropwise over 45 min.
After 12 h, the reaction mixture was cooled to 0° C. and the pH adjusted to 3-5 with aqueous ammonia solution.
The aqueous layer containing solid was washed with dichloromethane and acidified with 2N HCl, filtered and dried under vacuum to afford the title compound as brown solid (3.0 g, 44percent).
Reference: [1] Patent: WO2013/144737, 2013, A2, . Location in patent: Paragraph 252
[2] Patent: US2015/57309, 2015, A1, . Location in patent: Paragraph 0524
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4647 - 4654
[4] Chemistry - A European Journal, 2018, vol. 24, # 61, p. 16368 - 16378
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6138 - 6141
[6] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 151, p. 184 - 197
  • 2
  • [ 108166-03-6 ]
  • [ 635-80-3 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 21, p. 5420 - 5423
  • 3
  • [ 877-42-9 ]
  • [ 635-80-3 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 21, p. 5420 - 5423
  • 4
  • [ 123-73-9 ]
  • [ 150-13-0 ]
  • [ 635-80-3 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 817,819
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 817
  • 5
  • [ 877-43-0 ]
  • [ 635-80-3 ]
Reference: [1] Chemische Berichte, 1890, vol. 23, p. 2272
  • 6
  • [ 635-80-3 ]
  • [ 855763-77-8 ]
Reference: [1] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1932, vol. 110, p. 249,253
  • 7
  • [ 67-56-1 ]
  • [ 635-80-3 ]
  • [ 108166-01-4 ]
YieldReaction ConditionsOperation in experiment
59% at 0 - 65℃; for 12 h; Step 2: methyl 2-methylquinoline-6-carboxylate: To a solution of 2-methylquinoline-6- carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid ( 3ml) was added dropwise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59percent).
59% at 0 - 65℃; for 12 h; Step 2:
methyl 2-methylquinoline-6-carboxylate
To a solution of 2-methylquinoline-6-carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid (3 ml) was added dropwise at 0° C. and then stirred at 65° C. for 12 h.
The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added.
The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59percent).
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 929 - 931
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227[3] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4
[4] Patent: WO2013/144737, 2013, A2, . Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1, . Location in patent: Paragraph 0525
[6] Patent: WO2015/49535, 2015, A1, . Location in patent: Paragraph 00321
  • 8
  • [ 635-80-3 ]
  • [ 108166-01-4 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, p. 96 - 99[2] Zhurnal Obshchei Khimii, 1987, vol. 57, # 1, p. 113 - 117
  • 9
  • [ 635-80-3 ]
  • [ 141848-60-4 ]
Reference: [1] Patent: WO2014/108679, 2014, A1,
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