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[ CAS No. 1660963-42-7 ] {[proInfo.proName]}

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Chemical Structure| 1660963-42-7
Chemical Structure| 1660963-42-7
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Product Details of [ 1660963-42-7 ]

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 :

Calculated chemistry of [ 1660963-42-7 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.64
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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.77

Safety of [ 1660963-42-7 ]

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 [ 1660963-42-7 ]

* 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.

  • Downstream synthetic route of [ 1660963-42-7 ]

[ 1660963-42-7 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 331647-05-3 ]
  • N-(3-(2-((2,3-difluoro-4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide [ No CAS ]
  • 2
  • [ 1660979-94-1 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: trifluoroacetic acid / butan-1-ol / 90 °C
  • 3
  • [ 1660979-95-2 ]
  • [ 1660980-24-4 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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).
  • 4
  • [ 956100-62-2 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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
  • 5
  • [ 956100-63-3 ]
  • N-(3-(2-((2,3-difluoro-4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide [ No CAS ]
  • 6
  • [ 103-76-4 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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
  • 7
  • [ 771-69-7 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 1660980-23-3 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 20776-51-6 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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
  • 10
  • [ 331646-99-2 ]
  • N-(3-(2-((2,3-difluoro-4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide [ No CAS ]
  • 11
  • [ 30418-59-8 ]
  • [ 1660963-42-7 ]
YieldReaction ConditionsOperation 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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