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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 : |
|
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 |
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 |
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 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.97 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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. |