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[ CAS No. 451492-95-8 ] {[proInfo.proName]}

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Chemical Structure| 451492-95-8
Chemical Structure| 451492-95-8
Structure of 451492-95-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 451492-95-8 ]

CAS No. :451492-95-8 MDL No. :MFCD16038939
Formula : C27H28ClFN6O Boiling Point : -
Linear Structure Formula :- InChI Key :ZAJXXUDARPGGOC-UHFFFAOYSA-N
M.W : 507.00 Pubchem ID :9806229
Synonyms :

Calculated chemistry of [ 451492-95-8 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.3
Num. rotatable bonds : 6
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 150.63
TPSA : 73.39 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.73
Log Po/w (XLOGP3) : 4.54
Log Po/w (WLOGP) : 4.22
Log Po/w (MLOGP) : 3.75
Log Po/w (SILICOS-IT) : 4.57
Consensus Log Po/w : 4.36

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.78
Solubility : 0.000848 mg/ml ; 0.00000167 mol/l
Class : Moderately soluble
Log S (Ali) : -5.8
Solubility : 0.000797 mg/ml ; 0.00000157 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.13
Solubility : 0.00000378 mg/ml ; 0.0000000074 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.97

Safety of [ 451492-95-8 ]

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 [ 451492-95-8 ]

* 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 [ 451492-95-8 ]
  • Downstream synthetic route of [ 451492-95-8 ]

[ 451492-95-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 451494-30-7 ]
  • [ 79-10-7 ]
  • [ 451492-95-8 ]
YieldReaction ConditionsOperation in experiment
50% With N-[3-(diethylamino)propyl]-N'-ethylcarbodiimide hydrochloride; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; A solution of the amino compound 2a (6.08 g, 13.4 mmol) obtained by the method of Synthetic Example 2, acrylic acid (1.38 mL, 20.1 mmol), triethylamine (2.8 mL, 20.1 mmol) and EDC (3.86 g, 20.1 mmol) in DMF (100 mL) was stirred overnight at room temperature. Acrylic acid (0.46 mL, 6.71 mmol), triethylamine (0.93 mL, 6.71 mmol) and EDC (1.29. g, 6.71 mmol) were added to the reaction mixture and the mixture was further stirred overnight. The reaction mixture was poured into aqueous sodium hydrogen carbonate (300 mL) and the mixture was filtered. The residue was washed with water and water-ethanol and dried. The crudely purified substance was stirred with heating in water-ethanol and cooled to room temperature. The precipitate was collected by filtration and dried to give the objective compound 1a (3.41 g, 50percent). [CHEMMOL-00368] [0158] 1a: 1H NMR (DMSO-d6) δ ppm: 1.44 (s, 6H), 2.15 (s, 3H), 2.35 (br s, 4H), 2.64 (br s, 4H), 5.85 (d, J=10.3 Hz, 1H), 6.33 (d, J=16.9 Hz, 1H), 6.58 (dd, J=10.3, 16.9 Hz, 1H), 7.47 (t, J=9.1 Hz, 1H), 7.84 (br s, 2H), 8.20 (br d, J=6.1 Hz, 1H), 8.64 (s, 1H), 8.69 (s, 1H), 9.88 (s, 1H), 10.01 (s, 1H).
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 32-33
  • 2
  • [ 451494-30-7 ]
  • [ 79-10-7 ]
  • [ 814-68-6 ]
  • [ 451492-95-8 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine In tetrahydrofuran at 0 - 20℃; for 6 h; Example 6; Compound C (453 g, 1 mol) is dissolved in THF (2 L) and the solution is cooled to 0 0C. Acrylic acid (93.7 g, 1.3 mol, 1.3 equiv) and acryloyl chloride (108.6 g, 1.2 mol, 1.2 equiv) and triethylamine (253 g, 2.5 mol, 2.5 equiv) are added, and the resulting solution is stirred at 00C for 6 h and then allowed to warm to ambient temperature. Isolation and purification is carried out by solvent removal, trituration with isopropanol/water, and reslurrying acetonitrile. Compound D (324 - 350 g, 64 - 69percent yield)( 4-[N-3-chloro-4-fluorophenyl)]-7- [3-methyl-3-(4-methyl-l-piperazinyl)-l- butynyl]~6-[N-methyl acrylamide] quinazoline is thus isolated in >99percent purity.
Reference: [1] Patent: WO2007/103233, 2007, A2, . Location in patent: Page/Page column 15
  • 3
  • [ 948913-24-4 ]
  • [ 451492-95-8 ]
Reference: [1] Patent: WO2007/103233, 2007, A2, . Location in patent: Page/Page column 17
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