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CAS No. : | 211555-08-7 | MDL No. : | MFCD02683970 |
Formula : | C16H15N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BNDYIYYKEIXHNK-UHFFFAOYSA-N |
M.W : | 297.31 | Pubchem ID : | 5687 |
Synonyms : |
Janex 3
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 84.09 |
TPSA : | 76.5 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.98 cm/s |
Log Po/w (iLOGP) : | 2.46 |
Log Po/w (XLOGP3) : | 3.0 |
Log Po/w (WLOGP) : | 3.1 |
Log Po/w (MLOGP) : | 1.65 |
Log Po/w (SILICOS-IT) : | 2.2 |
Consensus Log Po/w : | 2.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.85 |
Solubility : | 0.0422 mg/ml ; 0.000142 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.27 |
Solubility : | 0.0159 mg/ml ; 0.0000536 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.57 |
Solubility : | 0.000804 mg/ml ; 0.0000027 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.53 |
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 |
---|---|---|
92% | 69 Example 69 Example 69 Using an analogous procedure to that described in Example 68, 4-chloro-6,7-dimethoxyquinazoline was reacted with 3-aminophenol to give 4-(3'-hydroxyanilino)-6,7-dimethoxyquinazoline in 92% yield, m.p. 256°-257° C. NMR Spectrum: 3.98 (s, 3H), 4.02 (s, 3H), 6.75 (m, 1H), 7.12 (d, 1H), 7.14 (d, 1H), 7.25 (t, 1H), 7.42 (s, 1H), 8.37 (s, 1H), 8.80 (s, 1H), 9.5 (broad hump, 1H), 11.4 (broad s, 1H); Elemental Analysis: Found C, 57.1; H, 4.8; N, 12.1; C16 H15 N3 O3. 1HCl. 0.25H2 O requires C, 56.8; H, 4.9; N, 12.4%. | |
claim 30 , wherein the quinazoline compound is selected from: 4-(3',5'-dibromo-4'-hydroxyphenyl)amino-6,7-dimethoxyquinazoline, 4-(4'-hydroxyphenyl)amino-6,7-dimethoxyquinazoline, 4-(3'-hydroxyphenyl)amino-6,7-dimethoxyquinazoline, 4-(2'-hydroxy-naphthyl-3')-amino-6,7-dimethoxyquinazoline, 4-{4'-[2"-(4"'-aminophenyl)-hexafluoropropyl]phenyl}-amino-6,7-dimethoxyquinazoline, and 4-(3'-trifluoromethoxylphenyl)-amino-6,7-dimethoxyquinazoline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium chloride; phenol In aq. buffer at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium sulfate; sodium citrate at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Heating; | General procedure for synthesis of quinazolines General procedure: 4-Chloro-6,7-dimethoxyquinazoline 3 and the required nucleophile were heated in solvent either thermally or using microwave heating until no further reaction was observed. On cooling, the hydrochloride salt was isolated by filtration. Alternative isolation procedures were employed if precipitation did not occur. Additional purification by preparative HPLC or flash column chromatography was employed in some cases. Spectroscopic data for compounds 4 [13], 6-9 [14-16], 20-21 [13], 25 [13], 28 [17] and 30 [18] are in agreement with those reported in the literature. |