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CAS No. : | 1256387-87-7 | MDL No. : | MFCD28386938 |
Formula : | C24H34BN3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MYPUONINDNZBTH-GMBSWORKSA-N |
M.W : | 439.36 | Pubchem ID : | 67506198 |
Synonyms : |
|
Num. heavy atoms : | 32 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 129.9 |
TPSA : | 76.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.02 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 4.17 |
Log Po/w (WLOGP) : | 3.62 |
Log Po/w (MLOGP) : | 2.32 |
Log Po/w (SILICOS-IT) : | 2.66 |
Consensus Log Po/w : | 2.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.07 |
Solubility : | 0.00375 mg/ml ; 0.00000853 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.49 |
Solubility : | 0.00143 mg/ml ; 0.00000325 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.6 |
Solubility : | 0.0011 mg/ml ; 0.00000251 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 5.61 |
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 |
---|---|---|
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4 h; Inert atmosphere | I. Preparation of Compound 613. A mixture of 3-(6-Bromo-1 H-benzoimidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2- carboxylic acid ferf-butyl ester 618 (264 mg, 0.673 mmol), benzene-1 ,4-diboronic acid dipinocal ester (5 eq., 3.36 g, 6.95 mmol), tetrakis(triphenylphosphine)palladium (5percent, 39 mg) and 2M potassium carbonate aqueous solution (3 eq., 1.01 ml_) in 5 mL DME was heated to 90°C under Ar for 4 hours. The reaction mixture was cooled and diluted in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer dried (MgS04), concentrated and purified by flash column chromatography (silica gel, 20 to 60percent ethyl acetate/hexane) to give 3-{6-[4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenyl]-1 H-benzoimidazol-2-yl}-2- aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 613 (295 mg, yield 85percent). LCMS- ESI": calc'd for C3oH38BN304: 515.45; Found: 516.1 (M+H+). |
85% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4 h; Inert atmosphere | I. Preparation of Compound 613 A mixture of 3-(6-Bromo-1H-benzoimidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 618 (264 mg, 0.673 mmol), benzene-1,4-diboronic acid dipinocal ester (5 eq., 3.36 g, 6.95 mmol), tetrakis(triphenylphosphine)palladium (5percent, 39 mg) and 2M potassium carbonate aqueous solution (3 eq., 1.01 mL) in 5 mL DME was heated to 90° C. under Ar for 4 hours. The reaction mixture was cooled and diluted in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 20 to 60percent ethyl acetate/hexane) to give 3-{6-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-benzoimidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 613 (295 mg, yield 85percent). LCMS-ES1-: calc'd for C30H38BN3O4: 515.45. Found: 516.1 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.16 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; for 3.5 h; Inert atmosphere | 1.08 g of compound 12, [1,1'-bis (diphenylphosphino) ferrocene] dichlorophenyl dichloromethane complex 114 mg,Fumarate borate 1.53 g,Potassium acetate 700mg,In the nitrogen under the protection of the reaction unit with a condensing device,Add 30 mL of boiled deoxygenated dioxane with stirring.Above the suspension of nitrogen protection in the 95 oil bath stir in the antiShould be 3.5 hours. Drying the reaction solution,Column chromatography (petroleum ether / ethyl acetate, 10: 1, 2: 1) gave product 13 as an off-white solid (1.16 g). |
26 g | With dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium; potassium acetate In 1,4-dioxane at 80 - 85℃; | (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester (25 g) was suspended in 1,4 dioxane (250 ml), followed by addition of bis(pinacolate) diboron (35.5 g), dichlorobis(di-tert- butylphenylphosphine)palladium(II) catalyst (1.5 g) and potassium acetate (18 g) at room temperature and allow to raise the temperature 80-85°C for 2-3 hours till it complies the reaction. The reaction completion is confirm by TLC, the solvent (1, 4 dioxane) was distilled out under reduced pressure and the reaction mass was cooled to room temperature by adding purified water and dichloromethane, to separate the layers. The organic layer was distilled out under reduced pressure to get a residue and further it is treated with cyclohexane to get a solid. Finally, the resultant solid was filtered and dried over at 40- 50°C to obtain a titled compound (26 g). |
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