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[ CAS No. 205448-64-2 ] {[proInfo.proName]}

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Chemical Structure| 205448-64-2
Chemical Structure| 205448-64-2
Structure of 205448-64-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 205448-64-2 ]

CAS No. :205448-64-2 MDL No. :MFCD26395147
Formula : C16H17NO7 Boiling Point : -
Linear Structure Formula :- InChI Key :FLQIWMCFHBVQGR-UHFFFAOYSA-N
M.W : 335.31 Pubchem ID :22646557
Synonyms :

Calculated chemistry of [ 205448-64-2 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.31
Num. rotatable bonds : 5
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 82.38
TPSA : 100.16 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 2.27
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 0.73
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.21 mg/ml ; 0.000625 mol/l
Class : Soluble
Log S (Ali) : -4.01
Solubility : 0.0328 mg/ml ; 0.0000977 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.055 mg/ml ; 0.000164 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.0

Safety of [ 205448-64-2 ]

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 [ 205448-64-2 ]

* 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 [ 205448-64-2 ]
  • Downstream synthetic route of [ 205448-64-2 ]

[ 205448-64-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 205448-64-2 ]
  • [ 417721-36-9 ]
Reference: [1] Patent: EP3293177, 2018, A1,
  • 2
  • [ 205448-64-2 ]
  • [ 205448-66-4 ]
Reference: [1] Patent: EP3293177, 2018, A1,
  • 3
  • [ 15568-85-1 ]
  • [ 27492-84-8 ]
  • [ 205448-64-2 ]
YieldReaction ConditionsOperation in experiment
96% at 50℃; for 0.666667 h; Heating / reflux The starting material was prepared as follows:
3-Methoxy-4-methoxycarbonylaniline (14.15 g, 78 mmol) was suspended in isopropanol and heated at 50° C. 2,2-Dimethyl-5-methoxymethylene-1,3-dioxane-4,6-dione (14.8 g, 80 mmol), (Montatsh. Chem. 1967, 98, 564), was then added in portions over 10 minutes and the mixture was heated at reflux for 30 minutes..
The mixture was left to cool to ambient temperature overnight..
The precipitate formed was collected by filtration, washed with isopropanol and dried under vacuum to give 5-((3-methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (25.2 g, 96percent).
95% at 70℃; for 1 h; Methyl 4-amino-2-methoxy-benzoate (1.07 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.0 g) were dissolved in 2-propanol (20 ml), and the mixture was stirred at 70°C for one hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with ether to give methyl 4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-2-methoxy-benzoate (1.71 g, yield 95percent). Methyl 4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino ]-2-methoxy-benzoate (1.70 g) and biphenyl (4.76 g) were suspended in diphenyl ether (15 ml), and the suspension was stirred at 240°C for one hr. The suspension was cooled to room temperature, and the precipitated crystal was collected by filtration and was washed with ether. The crystal thus obtained as such was used in the next reaction without further purification. N,N-Dimethylformamide (2 drops) was added to the crystal thus obtained. Further, phosphorus oxychloride (2.5 ml) was added thereto, and the mixture was stirred at 100°C for 2 hr. The solvent was removed by distillation under the reduced pressure, and water was added to the residue under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give methyl 4-chloro-7-methoxy-quinoline-6-carboxylate (707 mg, yield 55percent) (2 steps).
Reference: [1] Patent: US6809097, 2004, B1, . Location in patent: Page column 67
[2] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 48
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1649 - 1667
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1668 - 1680
  • 4
  • [ 2033-24-1 ]
  • [ 27492-84-8 ]
  • [ 149-73-5 ]
  • [ 205448-64-2 ]
YieldReaction ConditionsOperation in experiment
89.62% at 90℃; for 1 h; Methyl 2-methoxy-4-amino-benzoate (500.00 g, 2.76 mol), 2,2-dimethyl-1,3-dioxane-4,6-dione (397.73 g, 2.76 mol) and trimethyl orthoformate (292.84 g, 2.76 mol) were added to isopropanol (5.00 L). The reaction solution was heated up to an outer temperature of 90 °C and kept refluxing for 1 hour. The completion of the reaction was detected by TLC. The reaction solution was cooled to an outer temperature of 20 °C in an ice bath and then filtered. The solid was washed with MTBE (300 ml * 2) and then concentrated to dryness in a water bath. Compound 1A (873.00 g, 2.47 mol, the yield was 89.62percent and the purity was 95percent) was obtained as a light red powder. NMR (DMSO) demonstrated that the product was correct. 1H NMR (400 MHz, DMSO-d6) ppm 1.67 (s, 6 H) 3.76 (s, 3 H) 3.86 (s, 3 H) 7.19 (dd, J=8.41, 1.63 Hz, 1 H) 7.43 (d, J=1.25 Hz, 1 H) 7.71 (d, J=8.28 Hz, 1 H) 8.69 (d, J=10.04 Hz, 1 H) 11.25 (d, J=9.03 Hz, 1 H)
Reference: [1] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0199; 0200
  • 5
  • [ 15568-85-1 ]
  • [ 27492-84-8 ]
  • [ 205448-64-2 ]
  • [ 289707-57-9 ]
Reference: [1] Patent: US6630489, 2003, B1,
  • 6
  • [ 205448-64-2 ]
  • [ 205448-65-3 ]
YieldReaction ConditionsOperation in experiment
80% at 40 - 190℃; for 1 h; 5-((3-Methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10 g, 29.8 mmol) was suspended in DOWTHERM A, (trade mark of Fluka Chemie AG), (125 ml) and heated to 180-190° C. over 30 minutes..
The starting material dissolved at 100° C. and carbon dioxide came off at approximately 180° C.
The heating was stopped after a further 30 minutes and the product precipitated out as the temperature dropped..
Upon reaching 40° C. ether was added and the mixture was stirred for 30 minutes..
The solid was collected by filtration, washed with ether and dried under vacuum to give 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.56 g, 80percent).
11H NMR Spectrum: (DMSOd6) 3.80 (s, 3H); 3.85 (s, 3H); 5.95 (d, 1H); 7.00 (s, 1H); 7.85 (d, 1H); 8.40 (s, 1H); 11.6 (br s, 1H); MS-ESI: 234 [MH]+;
Reference: [1] Patent: US6809097, 2004, B1, . Location in patent: Page column 67
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1649 - 1667
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1668 - 1680
[4] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 48
[5] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0199; 0201
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