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CAS No. : | 1029684-37-4 | MDL No. : | MFCD11100960 |
Formula : | C14H23BN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BVIWGBKKGPHNAB-UHFFFAOYSA-N |
M.W : | 278.16 | Pubchem ID : | 24880008 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.79 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 78.16 |
TPSA : | 45.51 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 : | Yes |
Log Kp (skin permeation) : | -6.72 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.8 |
Log Po/w (WLOGP) : | 1.56 |
Log Po/w (MLOGP) : | 0.58 |
Log Po/w (SILICOS-IT) : | 0.86 |
Consensus Log Po/w : | 0.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.75 |
Solubility : | 0.493 mg/ml ; 0.00177 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.37 |
Solubility : | 1.17 mg/ml ; 0.00422 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.9 |
Solubility : | 0.346 mg/ml ; 0.00124 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 4.16 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogen In methanol at 0 - 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide at 130℃; for 0.666667h; Microwave irradiation; | 242 Example 242 (2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-9-(1-(tetrahydro-2H-pyran-2-yl)-1H-imidazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine 242 1-(Tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole was prepared by hydrogen with palladium reduction of 2-chloro-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole. To a mixture of 9-bromo-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine 250 mg, 0.67 mmol) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole (204 mg, 0.73 mmol) in dry DMF (2.5 mL) under nitrogen was added CsF (254 mg, 1.68 mmol), CuI (13 mg, 0.067 mmol) and Pd(PPh3)4 (39 mg, 0.034 mmol). The reaction mixture was heated at 130° C. for 40 min under microwave. Cooled to room temperature, the resulting mixture was poured into water and extracted with EtOAc. Dried organics over sodium sulfate and purified by pre-TLC (100% EtOAc) to give 242 as a yellow solid (49.3 mg, yield: 17%). 1H NMR (DMSO-d6, 400 MHz): δ8.49 (d, J=8.4 Hz, 1H), 8.11 (s, 1H), 7.97 (s, 1H), 7.92 (s, 1H), 7.28 (dd, J1=1.6 Hz, J2=8.4 Hz, 1H), 7.18 (d, J=6.8 Hz, 2H), 5.92-5.89 (m, 1H), 5.19 (d, J=9.2 Hz, 1H), 4.55-4.52 (m, 4H), 4.04 (d, J=11.2 Hz, 1H), 3.60-3.56 (m, 1H), 2.29-1.90 (m, 3H), 1.58-1.48 (m, 9H). MS: (ESI, m/z)=446 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16h; | 182A tert-butyl 4- { 2-oxo- 10-[ 1 -(tetrahydro-2H-pyran-2-yl)- 1 H-imidazol-5-yl] - 1 ,2-dihydropyrimido[ 1 ,2- b] indazol-4-yl Jpiperidine- 1 -carboxylate tert-butyl 4-( 10-bromo-2-oxo- 1 ,2-dihydropyrimido[ 1 ,2-b] indazol-4-yl)piperidine- 1 -carboxylate (200 mg, 0.45 mmol) and l-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH- imidazole (187 mg, 0.67 mmol) were dissolved in N,N-Dimethylformamide (5 ml) and treated with sodium carbonate solution (2M in water, 0.89 ml). After degassing the solution 1,1 '- Bis(diphenylphosphino)ferrocene-palladium(II)chloride (16.4 mg, 0.02 mmol) was added. After stirring at 80°C for 16 h, the mixture was separated via reverse phase HPLC (gradient acetonitrile/water with 0.1 % trifluoroacetic acid) which afforded the title compound (55.4 mg, 25% of theory). LC-MS (Method 5B): Rt = 0.84 min, MS (ESIPos): m z = 519.5 [M+H]+ |
55.4 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16h; | 182.A tert-butyl 4-{12-oxo-10-[1-(tetrahydro-2H-pyran-2-yl)-1H-imidazol-5-yl]-1,2-dihydropyrimido[1,2-b]indazol-4-yl}piperidine-1-carboxylate Example 182A tert-butyl 4-{12-oxo-10-[1-(tetrahydro-2H-pyran-2-yl)-1H-imidazol-5-yl]-1,2-dihydropyrimido[1,2-b]indazol-4-yl}piperidine-1-carboxylate tert-butyl 4-(10-bromo-2-oxo-1,2-dihydropyrimido[1,2-b]indazol-4-yl)piperidine-1-carboxylate (200 mg, 0.45 mmol) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole (187 mg, 0.67 mmol) were dissolved in N,N-Dimethylformamide (5 ml) and treated with sodium carbonate solution (2M in water, 0.89 ml). After degassing the solution 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)chloride (16.4 mg, 0.02 mmol) was added. After stirring at 80° C. for 16 h, the mixture was separated via reverse phase HPLC (gradient acetonitrile/water with 0.1% trifluoroacetic acid) which afforded the title compound (55.4 mg, 25% of theory). LC-MS (Method 5B): Rt=0.84 min, MS (ESIPos): m/z=519.5 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 95℃; Inert atmosphere; | A17 Preparation of intermediate 58 A solution of compound 277 (282 mg; 0.63 mmol), 1-(tetrahydro-2H-pyran-2-yl)-5- (4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-imidazo le (226 mg; 0.81 mmo 1) and K2C03 (173 mg; 1.25 mmol) in 1,4-dioxane (4.27 mL) and water (0.64 mL) was degassed under N2. Pd.C12(dppf).DCM (51 mg; 62.6 jimol) was added and the reaction mixture was heated at 95°C overnight. The resulting suspension was quenched withwater (10 mL) and extracted with EtOAc (3x20 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by chromatography over silica gel (irregular SiOH; 15-40 jim; 12 g; gradient: from 100% heptane to 90% EtOAc, 10% MeOH (+5% NH4OH)). The pure fractions were collected and the solvent was evaporated to give 127 mg (39%, brownsolid) of intermediate 58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere; | 84.1 Step 1 Into a 50-mL round-bottom flask, was placed 1-(3-[[1-chloro-8-methoxy-5-(4-methylbenzenesulfonyl)-5H-pyrido[4,3-b] indol-7-yl] oxy]propyl)pynolidine (200 mg, 0.39 mmol, 1eq.), dioxane (5 mL), water (1 mL), 1-(oxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1H-imidazole (130 mg, 0.47 mmol, 1.20 eq.), K2C03 (161 mg, 1.17 mmol, 3.00 eq.), Pd(PPh3)4 (23 mg, 0.02 mmol, 0.05 eq.). The resulting solution was stined for 16 hr at 100°C under N2. The reaction mixtures were combined and concentrated under vacuum. The product was subjected to reverse phasepreparative HPLC (Waters SunFire column, 19 x 150 mm; gradient elution of 20% MeCN in water to30% MeCN in water over a 10 mm period, where both solvents contain 0.05% TFA) to provide 8-methoxy-7-(3-(pynolidin- 1 -yl)propoxy)- 1 -(1 -(tetrahydro-2H-pyran-2-yl)- 1 H-imidazol-5-yl)-5-tosyl-5H-pyrido[4,3-b]indole (150 mg, 6 1%). MS (ESI, pos. ion) mlz: 630.3 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile at 150℃; for 0.75h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-t-butyl ether adduct; potassium carbonate In water; acetonitrile at 150℃; for 1h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 24h; |
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