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[ CAS No. 343787-29-1 ] {[proInfo.proName]}

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Chemical Structure| 343787-29-1
Chemical Structure| 343787-29-1
Structure of 343787-29-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 343787-29-1 ]

CAS No. :343787-29-1 MDL No. :MFCD11100329
Formula : C24H27N5O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DEEOXSOLTLIWMG-UHFFFAOYSA-N
M.W : 417.50 Pubchem ID :10158940
Synonyms :

Calculated chemistry of [ 343787-29-1 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 19
Fraction Csp3 : 0.33
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 125.72
TPSA : 78.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.56
Log Po/w (XLOGP3) : 3.26
Log Po/w (WLOGP) : 3.15
Log Po/w (MLOGP) : 2.24
Log Po/w (SILICOS-IT) : 2.62
Consensus Log Po/w : 2.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.54
Solubility : 0.012 mg/ml ; 0.0000288 mol/l
Class : Moderately soluble
Log S (Ali) : -4.58
Solubility : 0.011 mg/ml ; 0.0000262 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.62
Solubility : 0.000099 mg/ml ; 0.000000237 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.81

Safety of [ 343787-29-1 ]

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 [ 343787-29-1 ]

* 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 [ 343787-29-1 ]

[ 343787-29-1 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 610-81-1 ]
  • [ 343787-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / 72 h / Reflux 2.1: caesium carbonate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane; phenylboronic acid / 72 h / 115 °C 3.1: palladium dichloride; triethylamine; formic acid / 2 h / 65 °C 3.2: Reflux 4.1: 48 h / 20 °C 5.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 72 h / Reflux 5.2: 0.25 h / 20 °C
  • 2
  • [ 50982-75-7 ]
  • [ 343787-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane; phenylboronic acid / 72 h / 115 °C 2.1: palladium dichloride; triethylamine; formic acid / 2 h / 65 °C 2.2: Reflux 3.1: 48 h / 20 °C 4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 72 h / Reflux 4.2: 0.25 h / 20 °C
  • 3
  • [ 343788-53-4 ]
  • [ 343787-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: palladium dichloride; triethylamine; formic acid / 2 h / 65 °C 1.2: Reflux 2.1: 48 h / 20 °C 3.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 72 h / Reflux 3.2: 0.25 h / 20 °C
  • 4
  • [ 343788-55-6 ]
  • [ 343787-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 48 h / 20 °C 2.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 72 h / Reflux 2.2: 0.25 h / 20 °C
  • 5
  • [ 343787-31-5 ]
  • [ 73874-95-0 ]
  • [ 343787-29-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: trifluoro-methanesulfonic acid 2-[5-(2-methoxy-ethoxy)-benzoimidazol-1-yl]-quinolin-8-yl ester; tert-butyl piperidin-4-ylcarbamate With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl for 72h; Reflux; Stage #2: With trifluoroacetic acid at 20℃; for 0.25h;
  • 6
  • [ 343787-29-1 ]
  • [ 2134113-51-0 ]
YieldReaction ConditionsOperation in experiment
80% With N-chloro-succinimide; acetic acid; sodium iodide at 50℃; for 18h; Inert atmosphere; 1-{5-Iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine (IIQP) (13) A mixture of 12 N-chlorosuccinimide (NCS) (80mg, 0.6mmol, 1.2eq.) and 13 sodium iodide (NaI) (90mg, 0.6mmol, 1.2eq.) in 14 acetic acid (5mL) was added to 12 (209mg, 0.5mmol, 1.0eq.) in acetic acid (5mL) and the mixture was stirred at 50°C for 18h under nitrogen atmosphere. After adjusting pH to 9.0 using saturated 15 aqueous sodium bicarbonate (NaHCO3), the reaction mixture was extracted with dichloromethane (3×30mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (chloroform/methanol=50/1) to afford 13 (217mg, 80%) as a pale yellow solid. 1H NMR (400MHz, CDCl3): δ 1.76-1.85 (2H, m), 2.01-2.10 (2H, m), 2.85-2.96 (3H, m), 3.50 (3H, s), 3.82-3.84 (2H, m), 3.99 (2H, br d), 4.23-4.25 (2H, m), 7.00 (1H, d, J=8.0Hz), 7.26 (1H, dd, J=11.2, 2.0Hz), 7.38 (1H, d, J=2.0Hz), 7.74 (1H, d, J=9.2Hz), 7.98 (1H, d, J=8.0Hz), 8.39 (1H, d, J=9.2Hz), 8.56 (1H, d, J=9.2Hz), 8.68 (1H, s). 13C NMR (100MHz, CDCl3): δ 156.05, 150.46, 147.08, 145.51, 144.70, 142.19, 141.34, 137.42, 129.16, 126.68, 119.56, 114.91, 114.35, 113.68, 103.52, 88.63, 71.08, 67.77, 59.26, 51.44 (2C), 48.73, 36.28 (2C). HRMS (ESI+) calcd for C24H27IN5O2 [M+H+]: m/z=544.1204, found 544.1166
  • 7
  • [ 343787-29-1 ]
  • [ 2134119-89-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-chloro-succinimide; sodium iodide; acetic acid / 18 h / 50 °C / Inert atmosphere 2: triethylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere
  • 8
  • [ 343787-29-1 ]
  • [ 2135293-40-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-chloro-succinimide; sodium iodide; acetic acid / 18 h / 50 °C / Inert atmosphere 2: triethylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 24 h / Inert atmosphere; Reflux
  • 9
  • [ 343787-29-1 ]
  • [ 91487-18-2 ]
  • [ 2134106-60-6 ]
YieldReaction ConditionsOperation in experiment
77% With N-ethyl-N,N-diisopropylamine In dichloromethane at 50℃; for 2h; Inert atmosphere; N-3-Iodobenzoyl-1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-quinolin-8-yl}-piperidin-4-amine (IB-IQP) (18) A mixture of 12 (12mg, 30.0µmol, 1.0eq.), 29 N,N-diisopropylethylamine (DIPEA) (6µL, 33.0µmol, 1.1eq.), and 17 (11mg, 33.0µmol, 1.1eq.) in dry 19 dichloromethane (1mL) was stirred at 50°C for 2h under nitrogen atmosphere. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (chloroform/methanol=100/1) to afford 18 (15mg, 77%) as a colorless solid. 1H NMR (400MHz, DMSO-d6): δ 2.01-2.06 (4H, m), 2.86-2.91 (2H, m), 3.32 (3H, s), 3.71-3.73 (2H, m), 3.87 (2H, br d), 4.02 (1H, br s), 4.19-4.21 (2H, m), 7.31-7.38 (4H, m), 7.52 (1H, t, J=8.0Hz), 7.65 (1H, d, J=8.4Hz), 7.92 (2H, t, J=8.0Hz), 8.19 (1H, d, J=8.8Hz), 8.24 (1H, s), 8.56 (1H, d, J=8.4Hz), 8.64 (1H, d, J=8.0Hz), 8.95 (1H, d, J=8.8Hz), 9.19 (1H, s). 13C NMR (100MHz, CDCl3): δ 164.41, 155.56, 149.04, 146.97, 145.08, 142.42, 140.50, 140.34, 139.66, 136.95, 135.67, 130.48, 127.34, 126.97, 126.40, 126.31, 121.63, 118.35, 116.37, 114.21, 112.45, 102.76, 94.65, 70.52, 67.26, 58.22, 51.40 (2C), 47.18, 32.11 (2C). HRMS (ESI+), calcd for C31H31IN5O3 [M+H+]: m/z=648.1466, found 648.1468
  • 10
  • [ 112725-22-1 ]
  • [ 343787-29-1 ]
  • [ 2135293-41-1 ]
YieldReaction ConditionsOperation in experiment
56% With N-ethyl-N,N-diisopropylamine In dichloromethane at 50℃; for 3h; Inert atmosphere; N-3-(Tributylstannyl)-benzoyl-1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-quinolin-8-yl}-piperidin-4-amine (ATE-IQP) (19) The mixture of 12 (27mg, 73.0µmol, 1.0eq.), 32 DIPEA (15µL, 80.0µmol, 1.1eq.), and 16 (40mg, 80.0µmol, 1.1eq.) in dry 19 dichloromethane (3mL) was stirred at 50°C for 3h under nitrogen atmosphere. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (chloroform/methanol=100/1) to afford 19 (33mg, 56%) as a pale yellow solid. 1H NMR (400MHz, DMSO-d6): δ 0.84-0.88 (9H, m), 1.01-1.18 (6H, m), 1.26-1.35 (6H, m), 1.45-1.60 (6H, m), 2.03-2.06 (4H, m), 2.86-2.91 (2H, m), 3.31 (3H, s), 3.66-3.72 (2H, m), 3.88 (2H, br d), 4.03 (1H, br s), 4.17-4.18 (2H, m), 7.30-7.38 (3H, m), 7.46 (1H, t, J=7.2Hz), 7.52 (1H, t, J=8.0Hz), 7.60 (1H, d, J=7.6Hz), 7.65 (1H, d, J=7.2Hz), 7.81 (1H, d, J=8.0Hz), 7.91 (1H, s), 8.18 (1H, d, J=9.2Hz), 8.51 (1H, d, J=7.6Hz), 8.56 (1H, d, J=9.2Hz), 8.92 (1H, d, J=8.8Hz), 9.19 (1H, s). 13C NMR (100MHz, DMSO-d6): δ 166.56, 155.56, 149.08, 146.94, 145.12, 142.39, 141.39, 140.50, 140.31, 138.81, 135.13, 134.47, 127.60, 127.33, 126.94, 126.35, 126.29, 121.56, 118.27. 116.30, 114.26, 112.43, 102.68, 70.51, 67.21, 58.13, 51.40 (2C), 47.01, 32.21 (2C), 28.58 (3C), 26.68 (3C), 13.53 (3C), 9.21 (3C). HRMS (ESI+) calcd for C43H58N5O3Sn [M+H+]: m/z=812.3556, found 812.3573)
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