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[ CAS No. 254964-60-8 ] {[proInfo.proName]}

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Chemical Structure| 254964-60-8
Chemical Structure| 254964-60-8
Structure of 254964-60-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 254964-60-8 ]

CAS No. :254964-60-8 MDL No. :MFCD18251454
Formula : C20H17F3N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ONDYALNGTUAJDX-UHFFFAOYSA-N
M.W : 406.36 Pubchem ID :54682876
Synonyms :
ABR-215050

Calculated chemistry of [ 254964-60-8 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.2
Num. rotatable bonds : 5
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 102.1
TPSA : 71.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.09
Log Po/w (XLOGP3) : 3.51
Log Po/w (WLOGP) : 4.7
Log Po/w (MLOGP) : 2.64
Log Po/w (SILICOS-IT) : 3.28
Consensus Log Po/w : 3.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.65
Solubility : 0.00912 mg/ml ; 0.0000224 mol/l
Class : Moderately soluble
Log S (Ali) : -4.7
Solubility : 0.00809 mg/ml ; 0.0000199 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.71
Solubility : 0.000783 mg/ml ; 0.00000193 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.71

Safety of [ 254964-60-8 ]

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 [ 254964-60-8 ]

* 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.

  • Upstream synthesis route of [ 254964-60-8 ]
  • Downstream synthetic route of [ 254964-60-8 ]

[ 254964-60-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 22864-65-9 ]
  • [ 248282-18-0 ]
  • [ 254964-60-8 ]
YieldReaction ConditionsOperation in experiment
65% With thionyl chloride; triethylamine In dichloromethane EXAMPLE 8
N-Methyl-N-(4-trifluoromethyl-phenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide (Method B)
To an ice-cold solution of 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid (8 g, 0.032 mol), triethylamine (15.5 ml, 0.11 mol) and 4-trifluoromethyl-N-methylaniline (6.1 g, 0.035 mol) in 150 ml of methylene chloride was added dropwise during 0.5 hours a solution of thionyl chloride (3.0 ml, 0.042 mol) in 10 ml of methylene chloride.
The stirring was continued at 4° C. for 4 hours.
The solution was diluted with 10 ml of methylene chloride, washed with cold 1 M sulphuric acid and then extracted with 1 M sodium hydroxide.
The pH of the aqueous phase was adjusted to 8-8.5, clarified by filtration and then acidified with hydrochloric acid to pH 4.
On standing a crystalline precipitate was formed which was filtered off, washed with water and dried to give the title compound (8.5 g) yield 65percent.
1H NMR (CDCl3) δ 3.48 (3H, s), 3.54 (3H, s), 4.06 (3H, s), 6.70 (1H, d), 6.94 (1H, d), 7.46 (1H, t), 7.50 (4H, broad signal).
13C NMR (CDCl3) δ 29.8 (CH3), 36.9 (CH3), 56.9 (CH3), 103.5 (CH), 104.2 (C), 108.7 (CH), 109.5 (C), 117.3+121.7+126.0+130.3 (C), 125.8+125.9+125.9+126.0 (CH), 126.3 (CH), 127.9+128.4+128.9+129.4 (C), 131.8 (CH), 141.4 (C), 146.7 (C), 157.2 (C), 158.0 (C), 160.3 (C), 165.0 (C); some peaks are multiplets due to F-coupling. ESI MS/MS [M+H]+ 407, fragment 232.
65% With thionyl chloride; triethylamine In dichloromethane at 0 - 4℃; for 4.5 h; To an ice-cold solution of 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid (8 g, 0.032 mol), triethylamine (15.5 ml, 0.11 mol) and 4-trifluoromethyl-N-methylaniline (6.1 g, 0.035 mol) in 150 ml of methylene chloride was added dropwise during 0.5 hours a solution of thionyl chloride (3.0 ml, 0.042 mol) in 10 ml of methylene chloride. The stirring was continued at 4°C for 4 hours. The solution was diluted with 10 ml of methylene chloride, washed with cold 1 M sulphuric acid and then extracted with 1 M sodium hydroxide. The pH of the aqueous phase was adjusted to 8-8.5, clarified by filtration and then acidified with hydrochloric acid to pH 4. On standing a crystalline precipitate was formed which was filtered off, washed with water and dried to give the title compound (8.5 g) yield 65 percent. 1H NMR (CDCl3) δ 3.48 (3H, s), 3.54 (3H, s), 4,06 (3H, s), 6.70 (1H, d), 6.94 (1H, d), 7.46 (1H, t), 7.50 (4H, broad signal). 13C NMR (CDCl3) δ 29.8 (CH3), 36.9 (CH3), 56.9 (CH3), 103.5 (CH), 104.2 (C), 108.7 (CH), 109.5 (C), 117.3+121.7+126.0+130.3 (C), 125.8+125.9+125.9+126.0 (CH), 126.3 (CH), 127.9+128.4+128.9+129.4 (C), 131.8 (CH), 141.4 (C), 146.7 (C), 157.2 (C), 158.0 (C), 160.3 (C), 165,0 (C); some peaks are multiplets due to F-coupling. ESI MS/MS [M+H]+ 407, fragment 232.
Reference: [1] Patent: US6133285, 2000, A,
[2] Patent: EP1095021, 2003, B1, . Location in patent: Page/Page column 9
  • 2
  • [ 1354639-61-4 ]
  • [ 22864-65-9 ]
  • [ 254964-60-8 ]
YieldReaction ConditionsOperation in experiment
99% for 2 h; Reflux; Molecular sieve A mixture of 11 (5.00 g, 18.9 mmol), N-methyl-p-trifluoromethylaniline (5.13 g, 28.4 mmol) and n-octane (200 mL) were refluxed in a Soxhlet extraction apparatus containing 4A molecular sieves (22.9 g) for 2 hours. After cooling the mixture the product was isolated as above to furnish 7.6 g (99 percent) of 4-hydroxy-5-methoxy-N,l-dimethyl-2-oxo-N-[(4- trifluoromethyl)phenyl] - 1 ,2-dihydroquino line-3 -carboxamide (C) . 1 H-NMR analysis on the isolated product revealed no impurities other than 1 molpercent remaining ester 11. 1 H-NMR (CDCI3) 9.9 (s, 1H), 7.50 (bs, 4H), 7.46 (t, 1H), 6.94 (d, 1H), 6.70 (d, 1H), 4.06 (s, 3H), 3.54 (s, 3H), 3.48 (s, 3H). When the same reaction was performed by the traditional distillation from n-octane (Entry 26) during 2 hours according to prior art US patent No. 6,875,869 the product was isolated in 94 percent yield and determined by 1H-NMR analysis to consist of a mixture of compound C (96 molpercent) and the starting material 11 (4 molpercent).
Reference: [1] Patent: WO2012/4338, 2012, A1, . Location in patent: Page/Page column 13; 16
  • 3
  • [ 91105-97-4 ]
  • [ 254964-60-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
[2] Patent: EP1095021, 2003, B1,
  • 4
  • [ 22864-65-9 ]
  • [ 248282-13-5 ]
  • [ 254964-60-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
  • 5
  • [ 53600-33-2 ]
  • [ 254964-60-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
  • 6
  • [ 67765-42-8 ]
  • [ 254964-60-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088
  • 7
  • [ 254964-68-6 ]
  • [ 254964-60-8 ]
Reference: [1] Patent: EP1095021, 2003, B1,
  • 8
  • [ 1897-52-5 ]
  • [ 254964-60-8 ]
Reference: [1] Patent: EP1095021, 2003, B1,
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