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[ CAS No. 1375108-46-5 ] {[proInfo.proName]}

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Chemical Structure| 1375108-46-5
Chemical Structure| 1375108-46-5
Structure of 1375108-46-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1375108-46-5 ]

CAS No. :1375108-46-5 MDL No. :MFCD18205965
Formula : C14H17BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RJXJTNJULNSBLM-UHFFFAOYSA-N
M.W : 256.11 Pubchem ID :69093306
Synonyms :

Calculated chemistry of [ 1375108-46-5 ]      Expand+

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

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

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.83

Safety of [ 1375108-46-5 ]

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 [ 1375108-46-5 ]

* 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 [ 1375108-46-5 ]

[ 1375108-46-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 1375108-46-5 ]
  • [ 17341-93-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
In toluene at 0℃; for 0.5h; Schlenk technique;
  • 2
  • [ 1375108-46-5 ]
  • [ 2699771-72-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation 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
  • 3
  • [ 1375108-46-5 ]
  • [ 2699771-40-7 ]
YieldReaction ConditionsOperation 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
  • 4
  • [ 1375108-46-5 ]
  • [ 2756527-87-2 ]
  • [ 2756520-81-5 ]
YieldReaction ConditionsOperation 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)
  • 5
  • [ 1375108-46-5 ]
  • [ 2756527-88-3 ]
  • [ 2756520-82-6 ]
YieldReaction ConditionsOperation 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).
  • 6
  • [ 1375108-46-5 ]
  • [ 2756527-89-4 ]
  • [ 2756520-83-7 ]
YieldReaction ConditionsOperation 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)
  • 7
  • [ 7598-35-8 ]
  • [ 1375108-46-5 ]
  • [ 2756527-90-7 ]
YieldReaction ConditionsOperation 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)+]
  • 8
  • [ 7598-35-8 ]
  • [ 1375108-46-5 ]
  • [ 2756520-84-8 ]
YieldReaction ConditionsOperation 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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