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CAS No. : | 911227-46-8 | MDL No. : | MFCD07779179 |
Formula : | C16H25BN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KCJOSYVHWLABNF-UHFFFAOYSA-N |
M.W : | 304.19 | Pubchem ID : | 22831617 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 88.22 |
TPSA : | 51.66 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.47 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.37 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 0.81 |
Log Po/w (SILICOS-IT) : | 1.61 |
Consensus Log Po/w : | 1.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.09 |
Solubility : | 0.247 mg/ml ; 0.000811 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.1 |
Solubility : | 0.244 mg/ml ; 0.000803 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.48 |
Solubility : | 0.0101 mg/ml ; 0.0000331 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.15 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
52% | With potassium acetate In DMF (N,N-dimethyl-formamide); dichloromethane at 80℃; for 10h; | 1N Preparation of 1.7; To a solution OF BIS (PINACOLATO) diboron (1.14) (2. 18 g, 8.6 mmol, 1.2 eq) in N, N-DIMETHYLFORMAMIDE (10 mL) at 0°C was added potassium acetate (2.3 g, 23.4 mmol, 3.0 eq), L, L -BIS (diphenylphosphino) ferrocene palladium (II) chloride complex with dichloromethane (171 mg, 0.23 mmol, 0.03 eq). The reaction mixture was heated at 80°C at which point a solution of 1.13 (2.0 g, 7.8 mmol, 1. 0 EQ) IN NN- DIMETHYLFORMAMIDE (10 mL) was added dropwise. The reaction mixture was stirred at 80°C for another lOh. Ethyl acetate (75 ML) and water (50 mL) were added and the two phases were separated. The organic phase was washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a dark brown oil, which solidified to needles. The crude product was triturated with hexane. The resulting solid was collected by filtration. Yield: 52 °/0 IH NMR (400MHZ, CDC13) 8 8.92 (d, 1H), 8.14 (dd, 1H), 7.53 (d, 1H), 3.55 (q, 2H), 3.32 (q, 2H), 1.36 (s, 12H), 1.27 (t, 3H), 1.12 (t, 3H) |
52% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 0 - 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water for 10h; Heating / reflux; | 1N Preparation OF 1. 8B; To a solution of 1. 5a (1.48 g, 3.29 mmol, 1.0 eq) in dimethoxyethane (DME) (20 ML) under nitrogen was added sequentially a 2M aqueous solution of sodium carbonate (4.94 mL, 9.87 mmol, 3.0 EQ), lithium chloride (0.42 g, 9. 87 mmol, 3.0 eq), palladium (70 mg, 10 wt. % (dry basis) on activated carbon, 0.033 mmol, 0.01 eq), and 1.7 (1.0 g, 3.29 mmol, 1.0 eq). The mixture was heated under reflux for LOH. Dichloromethane (200 ML) was added to dilute the reaction mixture and palladium (O) on carbon was filtered off on a celite pad. The filtrate was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: hexane/ethyl acetate mixtures of increasing polarity). Yield: 76% H NMR (400MHZ, CDC13) 5 8.56 (dd, 1H), 7.75 (dd, 1H), 7.64 (dd, 1H), 7.22 (M, 1H), 6.99-6. 85 (M, 3H), 5.62 (s, 1H), 3.88 (M, 2H), 3.59 (q, 2H), 3.45 (q, 2H), 3.34 (M, 2H), 2.06 (M, 2H), 1.69 (M, 2H), 1. 48 (s, 9H), 1.29 (t, 3H), 1.20 (t, 3H) Mass Spectral Analysis IIILZ = 478.0 (M+H) + |
76% | With palladium 10% on activated carbon; sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water for 10h; Reflux; Inert atmosphere; | |
76% | With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water for 10h; Heating / reflux; | 1N.1.3 Preparation of 1.8b: To a solution of 1.5a (1.48 g, 3.29 mmol, 1.0 eq) in dimethoxyethane (DME) (20 mL) under nitrogen was added sequentially a 2M aqueous solution of sodium carbonate (4.94 mL, 9.87 mmol, 3.0 eq), lithium chloride (0.42 g, 9.87 mmol, 3.0 eq), palladium (70 mg, 10 wt. % (dry basis) on activated carbon, 0.033 mmol, 0.01 eq), and 1.7 (1.0 g, 3.29 mmol, 1.0 eq). The mixture was heated under reflux for 1Oh. Dichloromethane (200 mL) was added to dilute the reaction mixture and palladium(O) on carbon was filtered off on a celite pad. The filtrate was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. EPO The crude product was purified by column chromatography (eluent: hexane/ethyl acetate mixtures of increasing polarity).Yield: 76%1H NMR (400MHz, CDCl3) 5 8.56 (dd, IH), 7.75 (dd, IH), 7.64 (dd, IH), 7.22 (m,IH), 6.99-6.85 (m, 3H), 5.62 (s, IH), 3.88 (m, 2H), 3.59 (q, 2H), 3.45 (q, 2H), 3.34(m, 2H), 2.06 (m, 2H), 1.69 (m, 2H), 1.48 (s, 9H), 1.29 (t, 3H), 1.20 (t, 3H)Mass Spectral Analysis m/z = 478.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: bis(pinacol)diborane With potassium acetate In N,N-dimethyl-formamide at 0 - 80℃; Stage #2: 2-bromo-pyridine-2-carboxylic acid diethylamide In N,N-dimethyl-formamide at 80℃; for 10h; | 1N.1.9 Preparation of 1.7: To a solution of bis(ρinacolato)diboron (1.14) (2.18 g, 8.6 mmol, 1.2 eq) in N,N-dimethylformamide (10 mL) at O0C was added potassium acetate (2.3 g, 23.4 mmol, 3.0 eq), l,r-bis(diphenylphosphino)ferrocene palladium(II) chloride complex with dichloromethane (171 mg, 0.23 mmol, 0.03 eq). The reaction mixture was heated at 8O0C at which point a solution of 1.13 (2.0 g, 7.8 mmol, 1.0 eq) in N,N - dimethylformamide (10 mL) was added dropwise. The reaction mixture was stirred at 8O0C for another 1Oh. Ethyl acetate (75 mL) and water (50 mL) were added and the two phases were separated. The organic phase was washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a dark brown oil, which solidified to needles. The crude product was triturated with hexane. The resulting solid was collected by filtration. Yield: 52 %1H NMR (400MHz, CDCl3) 6 8.92 (d, IH), 8.14 (dd, IH), 7.53 (d, IH), 3.55 (q, 2H), 3.32 (q, 2H), 1.36 (s, 12H), 1.27 (t, 3H), 1.12 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dihydrogen peroxide In tetrahydrofuran; water for 1h; | 3.3 35% hydrogen peroxide water (0.17 mL, 1.97 mmol) was added dropwise to a tetrahydrofuran solution (3 mL) of the crude product provided by the above-mentioned reaction. The solution was stirred for 1 hour, follwed by adding ethyl acetate (10 mL), washing the organic layer with an aqueous 5% sodium thiosulfate solution and water, thereafter drying the layer with anhydrous sodium sulfate, and distilling this solvent away under reduced pressure. The obtained residue was purified by silica gel column chromatography (Purif-Pack SI60, hexane:ethyl acetate=l : 1) to obtain the title compound (250 mg, yield: 85%) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2’-bipyridine In hexane at 60℃; for 0.5h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: N,N-diethyl-2-pyridinecarboxamide With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In hexane at 20℃; for 18h; Sealed tube; | |
47% | With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 80℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate; lithium chloride / palladium 10% on activated carbon / 1,2-dimethoxyethane; water / 10 h / Heating / reflux 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 10 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Heating / reflux 2.1: tetrahydrofuran / 2 h / 20 °C 3.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 0 - 80 °C 3.2: 10 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; octylaluminum 3-([2,2'-bipyridin]-5-yl)-[1,1'-biphenyl]-2,2'-bis(olate) In tetrahydrofuran; hexane at 30℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: N,N-diethyl-2-pyridinecarboxamide In tetrahydrofuran; hexane at 30℃; for 18h; Inert atmosphere; Glovebox; Overall yield = 52 %; Overall yield = 32 mg; regioselective reaction; |
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