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[ CAS No. 100491-29-0 ] {[proInfo.proName]}

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Chemical Structure| 100491-29-0
Chemical Structure| 100491-29-0
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Product Details of [ 100491-29-0 ]

CAS No. :100491-29-0 MDL No. :MFCD01863285
Formula : C17H10ClF3N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :JLSXYCZRMYCIMY-UHFFFAOYSA-N
M.W : 382.72 Pubchem ID :1268243
Synonyms :

Calculated chemistry of [ 100491-29-0 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.12
Num. rotatable bonds : 4
Num. H-bond acceptors : 7.0
Num. H-bond donors : 0.0
Molar Refractivity : 88.31
TPSA : 61.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.18
Log Po/w (XLOGP3) : 4.05
Log Po/w (WLOGP) : 4.89
Log Po/w (MLOGP) : 3.54
Log Po/w (SILICOS-IT) : 4.73
Consensus Log Po/w : 4.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.96
Solubility : 0.00424 mg/ml ; 0.0000111 mol/l
Class : Moderately soluble
Log S (Ali) : -5.04
Solubility : 0.0035 mg/ml ; 0.00000914 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.8
Solubility : 0.0000608 mg/ml ; 0.000000159 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.67

Safety of [ 100491-29-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100491-29-0 ]

* 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 [ 100491-29-0 ]
  • Downstream synthetic route of [ 100491-29-0 ]

[ 100491-29-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 105152-47-4 ]
  • [ 100491-29-0 ]
YieldReaction ConditionsOperation in experiment
72.2% With trichlorophosphate In diethyl ether; chloroform; water; N,N-dimethyl-formamide (1)
Into 4 ml of N,N-dimethylformamide was dropped 250 mg of phosphorus oxychloride with ice-cooling, and 200 mg of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetate was added thereto after stirring at the same temperature for 10 minutes.
The resulting mixture was subjected to reaction at 50° to 60° C. for 3.5 hours.
The reaction mixture was poured into 50 ml of iced water, and 20 ml of chloroform was added thereto, after which the organic layer was separated, washed with 20 ml of water, and then dried over anhydrous magnesium sulfate.
The solvent was removed by distillation under reduced pressure, and to the residue thus obtained was added 5 ml of diethyl ether, after which crystals were collected by filtration to obtain 150 mg (yield 72.2percent) of ethyl 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate having a melting point of 217°-220° C.
This was recrystallized from an acetone-methanol mixture (1:1 by volume) to obtain crystals having a melting point of 219°-221° C.
Elementary analysis values for C17 H10 N2 O3 ClF3: Calcd. (percent): C, 53.35; H, 2.63; N, 7.32.
Found (percent): C, 53.61; H, 2.47; N, 6.96.
Reference: [1] Patent: US4704459, 1987, A,
  • 2
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YieldReaction ConditionsOperation in experiment
8 g With sodium hydride In tetrahydrofuran for 1.5 h; Inert atmosphere; Reflux A 60percent sodium hydride in oil suspension (1.73 g) was slowly added with stirring to a cold solution of nicotinylacrylate (5) (16.5 g) in THF (200 mL). The mixture was refluxed with stirring under nitrogen for 1.5 h, cooled, washed with water and dried yielding 8 g of (6). m.p.=210-212° C.
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2364 - 2369
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 518 - 525
[3] Patent: US2014/73631, 2014, A1, . Location in patent: Paragraph 0128; 0133
  • 3
  • [ 96568-04-6 ]
  • [ 100491-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2364 - 2369
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 518 - 525
[3] Patent: US2014/73631, 2014, A1,
  • 4
  • [ 96568-02-4 ]
  • [ 100491-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2364 - 2369
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 518 - 525
[3] Patent: US2014/73631, 2014, A1,
  • 5
  • [ 82671-06-5 ]
  • [ 100491-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2364 - 2369
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 518 - 525
[3] Patent: US2014/73631, 2014, A1,
  • 6
  • [ 82671-03-2 ]
  • [ 100491-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 11, p. 2364 - 2369
[2] Patent: US2014/73631, 2014, A1,
  • 7
  • [ 367-25-9 ]
  • [ 100491-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 518 - 525
  • 8
  • [ 96568-05-7 ]
  • [ 100491-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 518 - 525
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