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CAS No. : | 1660963-42-7 | MDL No. : | MFCD30345533 |
Formula : | C29H28F2N6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IDRGFNPZDVBSSE-UHFFFAOYSA-N |
M.W : | 530.57 | Pubchem ID : | 117909640 |
Synonyms : |
|
Num. heavy atoms : | 39 |
Num. arom. heavy atoms : | 22 |
Fraction Csp3 : | 0.21 |
Num. rotatable bonds : | 9 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 155.31 |
TPSA : | 93.62 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.51 cm/s |
Log Po/w (iLOGP) : | 3.89 |
Log Po/w (XLOGP3) : | 4.26 |
Log Po/w (WLOGP) : | 4.45 |
Log Po/w (MLOGP) : | 3.11 |
Log Po/w (SILICOS-IT) : | 4.36 |
Consensus Log Po/w : | 4.01 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.64 |
Solubility : | 0.00122 mg/ml ; 0.00000231 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.94 |
Solubility : | 0.000612 mg/ml ; 0.00000115 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -9.22 |
Solubility : | 0.000000319 mg/ml ; 0.0000000006 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.77 |
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 |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: trifluoroacetic acid / butan-1-ol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.5% | With trifluoroacetic acid In butan-1-ol at 90℃; | 153 Preparation of N-(3-(2-((2,3-difluoro-4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide To a suspension of 2-(4-(4-amino-2,3-difiuorophenyl)piperazin-l-yl)ethanol (83 mg, 0.32 mmol, 1 eq.) and N-(3-(2-chloroquinazolin-8-yl)phenyl)acrylamide (100 mg, 0.32 mmol, 1 eq.) in n-BuOH (5 mL) was added TFA (68 mg, 0.64 mmol, 2 eq.) and the resulting mixture was stirred at 90 °C overnight. The mixture was concentrated, diluted with DCM (20 mL) ,washed with Na2C03 solution (20 mL), dried over anhydrous Na2S04, concentrated and the residue was purified via column chromatography (MeOH/DCM=l/30, v:v) to afford N-(3-(2-((2,3-difiuoro-4-(4-(2-hydroxyethyl)piperazin-l-yl)phenyl)amino)quinazolin-8- yl)phenyl)acrylamide as a yellow solid (16.3 mg, 9.5% yield). LRMS (M+H+) m/z calculated 531.2, found 531.2.1H NMR (CD3OD, 400 MHz) δ 9.21 (s, 1 H), 7.19-8.01 (m, 10 H), 8.90 (s, 1 H), 6.41-6.49 (m, 3 H), 5.86 (m, 1 H), 3.98-4.01 (m, 3 H), 3.70-3.76 (m, 3 H), 3.40-3.49 (m, 2 H), 3.37-3.39 (m, 4 H), 3.18 (m, 2H). |
9.5% | With trifluoroacetic acid In butan-1-ol at 90℃; | 1 Example 1: Preparation of the compound of Formula I (N-(3-(2-((2,3-difluoro-4-(4-(2- hydroxyethyl)piperazin-l-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide) [0257] To a suspension of 2-(4-(4-amino-2,3-difluorophenyl)piperazin-l-yl)ethanol (83 mg, (0371) 0.32 mmol, 1 eq.) and N-(3-(2-chloroquinazolin-8-yl)phenyl)acrylamide (100 mg, 0.32 mmol, 1 eq.) in n-BuOH (5 mL) was added TFA (68 mg, 0.64 mmol, 2 eq.) and the resulting mixture was stirred at 90 °C overnight. The mixture was concentrated, diluted with DCM (20 mL) , washed with Na2C03 solution (20 mL), dried over anhydrous Na2S04, concentrated and the residue was purified via column chromatography (MeOH/DCM=l/30, v:v) to afford N-(3-(2-((2,3-difluoro-4- (4-(2-hydroxyethyl)piperazin-l-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide as a yellow solid(l6.3 mg, 9.5% yield). LRMS (M+H+) m/z calculated 531.2, found 531.2. 1H NMR (0372) (CD3OD, 400 MHz) d 9.21 (s, 1 H), 7.19-8.01 (m, 10 H), 8.90 (s, 1 H), 6.41-6.49 (m, 3 H), 5.86 (m, 1 H), 3.98-4.01 (m, 3 H), 3.70-3.76 (m, 3 H), 3.40-3.49 (m, 2 H), 3.37-3.39 (m, 4 H), 3.18 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: isopentyl nitrite / tetrahydrofuran / 12 h / 70 °C 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere 3: triethylamine / dichloromethane / 1 h / 20 °C 4: trifluoroacetic acid / butan-1-ol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / methanol / 20 °C 3: trifluoroacetic acid / butan-1-ol / 90 °C | ||
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / methanol / 20 °C 3: trifluoroacetic acid / butan-1-ol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / methanol / 20 °C 3: trifluoroacetic acid / butan-1-ol / 90 °C | ||
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / methanol / 20 °C 3: trifluoroacetic acid / butan-1-ol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C 2: trifluoroacetic acid / butan-1-ol / 90 °C | ||
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C 2: trifluoroacetic acid / butan-1-ol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 3 h / 200 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 12 h / 130 °C 3: ammonium hydroxide / tetrahydrofuran / 0.5 h / 0 °C 4: isopentyl nitrite / tetrahydrofuran / 12 h / 70 °C 5: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 12 h / 80 °C / Inert atmosphere 6: triethylamine / dichloromethane / 1 h / 20 °C 7: trifluoroacetic acid / butan-1-ol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 12 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice 3: trifluoroacetic acid / butan-1-ol / 90 °C |
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