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CAS No. : | 1375108-46-5 | MDL No. : | MFCD18205965 |
Formula : | C14H17BN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RJXJTNJULNSBLM-UHFFFAOYSA-N |
M.W : | 256.11 g/mol | Pubchem ID : | 69093306 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 76.01 |
TPSA : | 44.24 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.53 |
Log Po/w (WLOGP) : | 1.93 |
Log Po/w (MLOGP) : | 1.0 |
Log Po/w (SILICOS-IT) : | 1.8 |
Consensus Log Po/w : | 1.45 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.35 |
Solubility : | 0.116 mg/ml ; 0.000452 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.11 |
Solubility : | 0.201 mg/ml ; 0.000784 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.93 |
Solubility : | 0.003 mg/ml ; 0.0000117 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.83 |
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: |
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* 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 |
---|---|---|
In toluene at 0℃; for 0.5h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 0.5 h / 0 °C / Schlenk technique 2: (1R,2R)-1,2-bis(4-(3-(1-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)-5-(3-methoxy-3-methylbut-1-yn-1-yl)phenyl)-1H-1,2,3-triazol-1-yl)cyclohexane / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 0.5 h / 0 °C / Schlenk technique 2: (1R,2R)-1,2-bis(4-(3-(1-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)-5-(3-methoxy-3-methylbut-1-yn-1-yl)phenyl)-1H-1,2,3-triazol-1-yl)cyclohexane / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.64% | With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; Inert atmosphere; | 15.2 Step 2-2-fluoro-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide To a solution of N-(2-bromo-4-pyridyl)-2-fluoro-prop-2-enamide (40 mg, 163.23 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (50.2 mg, 195.88 μmol, 1.2 eq) in dioxane (2 mL) and H2O (0.25) was added Cs2CO3 (159.6 mg, 489.7 μmol, 3 eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium;dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (6.9 mg, 8.16 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (7.6 mg, 16.32 μmol, 0.1 eq) under N2. The reaction mixture was stirred at 95 °C for 1 h. The reaction mixture was poured into saturated EDTA (20 mL) and stirred for 60 min. The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic phase was washed with brine (3 x 20 mL), dried with anhydrous Na2SO4, filtered, and concentrated in vacuo to afford a residue. The residue was purified by prep-HPLC to afford the title compound 2-fluoro-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide (18.6 mg, 63.07 μmol, 38.64% yield, 99.795% purity) as a white solid.295.1.1H NMR (400MHz, DMSO-d6) δ = 9.67 (s, 1H), 9.36 (s, 1H), 8.71 (d, J=5.6 Hz, 1H), 8.54 (s, 2H), 8.43 (dd, J=1.6, 8.4 Hz, 1H), 8.31 (d, J=8.4 Hz, 1H), 7.89 (dd, J=2.0, 5.6 Hz, 1H), 5.93-5.74 (m, 1H), 5.57 (dd, J=4.0, 15.6 Hz, 1H) |
38.64% | With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; Inert atmosphere; | 15.2 Step 2-2-fluoro-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide To a solution of N-(2-bromo-4-pyridyl)-2-fluoro-prop-2-enamide (40 mg, 163.23 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (50.2 mg, 195.88 μmol, 1.2 eq) in dioxane (2 mL) and H2O (0.25) was added Cs2CO3 (159.6 mg, 489.7 μmol, 3 eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium;dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (6.9 mg, 8.16 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (7.6 mg, 16.32 μmol, 0.1 eq) under N2. The reaction mixture was stirred at 95 °C for 1 h. The reaction mixture was poured into saturated EDTA (20 mL) and stirred for 60 min. The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic phase was washed with brine (3 x 20 mL), dried with anhydrous Na2SO4, filtered, and concentrated in vacuo to afford a residue. The residue was purified by prep-HPLC to afford the title compound 2-fluoro-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide (18.6 mg, 63.07 μmol, 38.64% yield, 99.795% purity) as a white solid.295.1.1H NMR (400MHz, DMSO-d6) δ = 9.67 (s, 1H), 9.36 (s, 1H), 8.71 (d, J=5.6 Hz, 1H), 8.54 (s, 2H), 8.43 (dd, J=1.6, 8.4 Hz, 1H), 8.31 (d, J=8.4 Hz, 1H), 7.89 (dd, J=2.0, 5.6 Hz, 1H), 5.93-5.74 (m, 1H), 5.57 (dd, J=4.0, 15.6 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22.6% | With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; Inert atmosphere; | 15.2 Step 2 - (E)-N-(2-quinazolin-7-yl-4-pyridyl)but-2-enamide To a solution of (E)-N-(2-bromo-4-pyridyl)but-2-enamide (40 mg, 165.92 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (63.7 mg, 248.88 μmol, 1.5 eq), in dioxane (2 mL) and H2O (0.5 mL) was added Cs2CO3(162.2 mg, 497.75 μmol, 3 eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (7 mg, 8.3 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxy phenyl)phenyl]phosphane (7.7 mg, 16.59 μmol, 0.1 eq) under N2. The mixture was stirred at 95 °C for 1 h. The reaction mixture was poured into saturated EDTA (30 mL) and stirred for 60 min. The aqueous phase was extracted with EtOAc (3 x 15 mL). The combined organic layer was washed with brine (3 x 15 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to afford the title compound (E)-N-(2-quinazolin-7-yl-4-pyridyl) but-2-enamide (10.9 mg, 37.5 μmol, 22.60% yield, 99.876% purity) as a white solid.291.1.1H NMR (400MHz, DMSO-d6) δ = 10.51 (s, 1H), 9.67 (s, 1H), 9.36 (s, 1H), 8.64 (d, J=5.6 Hz, 1H), 8.51 (s, 1H), 8.44-8.38 (m, 2H), 8.29 (d, J=8.4 Hz, 1H), 7.69 (dd, J=2.0, 5.6 Hz, 1H), 6.96-6.90 (m, 1H). |
22.6% | With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; Inert atmosphere; | 15.2 Step 2 - (E)-N-(2-quinazolin-7-yl-4-pyridyl)but-2-enamide To a solution of (E)-N-(2-bromo-4-pyridyl)but-2-enamide (40 mg, 165.92 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (63.7 mg, 248.88 μmol, 1.5 eq), in dioxane (2 mL) and H2O (0.5 mL) was added Cs2CO3(162.2 mg, 497.75 μmol, 3 eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (7 mg, 8.3 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxy phenyl)phenyl]phosphane (7.7 mg, 16.59 μmol, 0.1 eq) under N2. The mixture was stirred at 95 °C for 1 h. The reaction mixture was poured into saturated EDTA (30 mL) and stirred for 60 min. The aqueous phase was extracted with EtOAc (3 x 15 mL). The combined organic layer was washed with brine (3 x 15 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to afford the title compound (E)-N-(2-quinazolin-7-yl-4-pyridyl) but-2-enamide (10.9 mg, 37.5 μmol, 22.60% yield, 99.876% purity) as a white solid.291.1.1H NMR (400MHz, DMSO-d6) δ = 10.51 (s, 1H), 9.67 (s, 1H), 9.36 (s, 1H), 8.64 (d, J=5.6 Hz, 1H), 8.51 (s, 1H), 8.44-8.38 (m, 2H), 8.29 (d, J=8.4 Hz, 1H), 7.69 (dd, J=2.0, 5.6 Hz, 1H), 6.96-6.90 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20.93% | With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; | 15.2 Step 2-2-methyl-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide To a solution of N-(2-bromo-4-pyridyl)-2-methyl-prop-2-enamide (50 mg, 207.4 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (53.1 mg, 207.4 μmol, 1 eq) in dioxane (2 mL), H2O (0.25) was added Cs2CO3(202.7 mg, 622.19 μmol, 3 eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (8.7 mg, 10.37 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxy phenyl) phenyl]phosphane (9.7 mg, 20.74 μmol, 0.1 eq). The reaction mixture was stirred at 95 °C for 1 h. The reaction mixture was poured into saturated EDTA (20 mL) and stirred for 60 min. The aqueous phase was extracted with EtOAc (3 x 15 mL). The combined organic layer was washed with brine (3 x 20 mL), dried over anhydrous Na2SO4,filtered, and concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to afford the title compound 2-methyl-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide (12.6 mg, 43.4 μmol, 20.93% yield, 100.0% purity) as a white solid.291.1.1H NMR (400MHz, DMSO-d6) δ = 10.40(br, s, 1H), 9.67 (s, 1H), 9.36 (s, 1H), 8.66 (d, J=5.6 Hz, 1H), 8.53 (s, 1H), 8.50 (d, J=1.6 Hz, 1H), 8.42 (dd, J=1.6, 8.8 Hz, 1H), 8.30 (d, J=8.8 Hz, 1H), 7.85 (dd, J=2.0, 5.6 Hz, 1H), 5.95 (s, 1H), 5.68 (d, J=1.2 Hz, 1H), 2.00 (s, 3H) |
20.93% | With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; | 15.2 Step 2-2-methyl-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide To a solution of N-(2-bromo-4-pyridyl)-2-methyl-prop-2-enamide (50 mg, 207.4 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (53.1 mg, 207.4 μmol, 1 eq) in dioxane (2 mL), H2O (0.25) was added Cs2CO3(202.7 mg, 622.19 μmol, 3 eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl]phosphane (8.7 mg, 10.37 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxy phenyl) phenyl]phosphane (9.7 mg, 20.74 μmol, 0.1 eq). The reaction mixture was stirred at 95 °C for 1 h. The reaction mixture was poured into saturated EDTA (20 mL) and stirred for 60 min. The aqueous phase was extracted with EtOAc (3 x 15 mL). The combined organic layer was washed with brine (3 x 20 mL), dried over anhydrous Na2SO4,filtered, and concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to afford the title compound 2-methyl-N-(2-quinazolin-7-yl-4-pyridyl)prop-2-enamide (12.6 mg, 43.4 μmol, 20.93% yield, 100.0% purity) as a white solid.291.1.1H NMR (400MHz, DMSO-d6) δ = 10.40(br, s, 1H), 9.67 (s, 1H), 9.36 (s, 1H), 8.66 (d, J=5.6 Hz, 1H), 8.53 (s, 1H), 8.50 (d, J=1.6 Hz, 1H), 8.42 (dd, J=1.6, 8.8 Hz, 1H), 8.30 (d, J=8.8 Hz, 1H), 7.85 (dd, J=2.0, 5.6 Hz, 1H), 5.95 (s, 1H), 5.68 (d, J=1.2 Hz, 1H), 2.00 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; Inert atmosphere; | 15.1 Step 1-2-quinazolin-7-ylpyridin-4-amine To a solution of 2-bromopyridin-4-amine (100 mg, 578 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (162.8 mg, 635.8 μmol, 1.1 eq) in dioxane (4 mL), H2O (1 mL) was added Cs2CO3 (565 mg, 1.73 mmol, 3.0eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[2-(2,6-diisopropoxyphenyl)phenyl]phosphane (24.2 mg, 28.9 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl] phosphane (27 mg, 57.8 μmol, 0.1 eq) under N2. The reaction mixture was stirred at 95 °C for 1 h. LCMS showed ~10% of the starting material remained. The reaction mixture was poured into saturated EDTA (20 mL) and stirred for 1 h. The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (3 x 20 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a residue. The residue was washed with DCM (3 x 5 mL) to afford the title compound 2-quinazolin-7-ylpyridin-4-amine (80 mg, crude) as a light yellow solid. LC-MS(ES+, m/z) 223.2 [(M+H)+] | |
With methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In 1,4-dioxane; water monomer at 95℃; for 1h; Inert atmosphere; | 15.1 Step 1-2-quinazolin-7-ylpyridin-4-amine To a solution of 2-bromopyridin-4-amine (100 mg, 578 μmol, 1 eq), 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline (162.8 mg, 635.8 μmol, 1.1 eq) in dioxane (4 mL), H2O (1 mL) was added Cs2CO3 (565 mg, 1.73 mmol, 3.0eq), [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl-[2-(2,6-diisopropoxyphenyl)phenyl]phosphane (24.2 mg, 28.9 μmol, 0.05 eq) and dicyclohexyl-[2-(2,6-diisopropoxyphenyl) phenyl] phosphane (27 mg, 57.8 μmol, 0.1 eq) under N2. The reaction mixture was stirred at 95 °C for 1 h. LCMS showed ~10% of the starting material remained. The reaction mixture was poured into saturated EDTA (20 mL) and stirred for 1 h. The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with brine (3 x 20 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a residue. The residue was washed with DCM (3 x 5 mL) to afford the title compound 2-quinazolin-7-ylpyridin-4-amine (80 mg, crude) as a light yellow solid. LC-MS(ES+, m/z) 223.2 [(M+H)+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine; methanesulfonato (2-dicyclohexylphosphino-2’,6’- di-isopropoxy-1,1‘-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl)palladium(II); Cs2CO3 / 1,4-dioxane; water monomer / 1 h / 95 °C / Inert atmosphere 2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1 h / 0 °C |
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