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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 : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.81 |
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 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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) |