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CAS No. : | 1003043-55-7 | MDL No. : | MFCD07375134 |
Formula : | C6H9BN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VTPBKJXRYUDPAJ-UHFFFAOYSA-N |
M.W : | 167.96 | Pubchem ID : | 16427142 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.16 |
TPSA : | 75.47 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.48 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | -0.22 |
Log Po/w (WLOGP) : | -1.44 |
Log Po/w (MLOGP) : | -1.62 |
Log Po/w (SILICOS-IT) : | -1.36 |
Consensus Log Po/w : | -0.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.91 |
Solubility : | 20.4 mg/ml ; 0.122 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.91 |
Solubility : | 20.8 mg/ml ; 0.124 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.07 |
Solubility : | 14.3 mg/ml ; 0.0853 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.22 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
In 1,4-dioxane; | Example 283 7-(2-Ethoxy-pyrimidin-5-yl)-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 281 using <strong>[1003043-55-7]2-ethoxypyrimidin-5-ylboronic acid</strong> (16.7 mg, 0.1 mmol) dissolved in dioxane (0.3 mL) instead of 5-cyanothiophen-2-ylboronic acid (15.3 mg, 0.1 mmol) dissolved in dioxane (0.3 mL). Yield: 10 mg, 29%. 1H NMR (400 MHz, DMSO/D2O) delta ppm 8.59 (s, 2H) 8.29 (d, J=8.54 Hz, 1H) 7.83-7.96 (m, 2H) 7.62-7.74 (m, 3H) 7.53-7.58 (m, 1 H) 7.49 (d, J=8.54 Hz, 1H) 7.42-7.46 (m, 1H) 4.55 (s, 2H) 4.37-4.44 (m, 2H) 3.98 (t, J=7.17 Hz, 2H) 3.28 (t, J=7.17 Hz, 2H) 1.37 (t, J=7.02 Hz, 3H); MS (ESI) m/z 411 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; | Example 327 4-(2-Ethoxy-pyrimidin-5-yl)-6-(2-quinolin-2-yl-ethyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one The title compound was prepared in analogy to the process described in Example 322 but using <strong>[1003043-55-7]2-ethoxypyrimidin-5-ylboronic acid</strong> (16.8 mg, 0.1 mmol) dissolved in dioxane (0.35 mL) instead of 3-methylpyridin-4-ylboronic acid (13.7 mg, 0.1 mmol) dissolved in dioxane (0.35 mL). Yield: 2.7 mg, 8%. 1H NMR (500 MHz, DMSO/D2O) delta ppm 8.75-8.79 (m, 3H) 8.29 (d, J=8.24 Hz, 1H) 7.94 (d, J=7.02 Hz, 1H) 7.82 (d, J=8.54 Hz, 1H) 7.68-7.73 (m, 1H) 7.49-7.57 (m, 3H) 4.61 (s, 2H) 4.43 (q, J=7.02 Hz, 2H) 4.03 (t, J=7.17 Hz, 2H) 3.31 (t, J=7.17 Hz, 2H) 1.37 (t, J=7.02 Hz, 3H); MS (ESI) m/z 412 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; | Example 343 4-(2-Ethoxy-pyrimidin-5-yl)-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 341 but using <strong>[1003043-55-7]2-ethoxypyrimidin-5-ylboronic acid</strong> (16.8 mg, 0.1 mmol) dissolved in dioxane (0.35 mL) instead of 2-(dimethylamino)pyrimidin-5-ylboronic acid (16.7 mg, 0.1 mmol) dissolved in dioxane (0.35 mL). Yield: 3.2 mg, 9%. 1H NMR (500 MHz, DMSO/D2O) delta ppm 8.85 (s, 2H) 8.28 (d, J=8.24 Hz, 1H) 7.91 (dd, J=15.41, 8.09 Hz, 2 H) 7.69-7.76 (m, 3H) 7.63 (t, J=7.48 Hz, 1H) 7.54-7.59 (m, 1H) 7.51 (d, J=8.24 Hz, 1H) 4.76 (s, 2H) 4.45 (q, J=7.02 Hz, 2H) 4.02 (t, J=7.32 Hz, 2H) 3.30 (t, J=7.32 Hz, 2H) 1.39 (t, J=7.02 Hz, 3H); MS (ESI) m/z 411 (M+H)+. MS (APCI) m/z 411 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium carbonate; In acetonitrile; at 140.0℃; for 0.333333h;Inert atmosphere; Microwave irradiation; | To a glass vial was added 2-methoxypyrimidine-5-boronic acid (0.105 g, 0.613 mmol), (2- chloropyrimidin-4-yl)-(l-isopropyl-lH-imidazo[4,5-c]pyridin-6-yl)amine (Example 12, Step 4) (0.176 mg, 0.613 mmol), Pd(Amphos)2Cl2 (22 mg, 0.031 mmol), a 2M solution of Na2C03 (0.46 mL, 0.92 mmol) and acetonitnle (2.5 mL). The mixture was degassed by nitrogen bubbling for 20 min. The reaction vial was sealed and heated in a microwave at 140 C for 20 min. Alternatively, the reaction was sealed and stirred at 100 C in an oil bath for 2 h. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude product was purified by reverse- phase HPLC and lyophilized to give the title compound (41 mg, 18%). LCMS (ESI): RT 3.91 min, [M+H]+ 377.2, method = B; lH NMR (400 MHz, DMSO-d6) delta 10.31 (s, 1H), 9.40 (s, 2H), 8.73 (d, J= 1.0 Hz, 1H), 8.46 (d, J= 5.9 Hz, 1H), 8.39 (d, J= 7.9 Hz, 2H), 7.30 (s, 1H), 4.85 - 4.71 (m, 1H), 4.46 (q, J= 7.1 Hz, 2H), 1.61 (d, J= 6.8 Hz, 6H), 1.38 (t, J= 7.1 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.35 g | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In acetonitrile; at 80.0℃;Inert atmosphere; | A mixture of intermediate 17.7 (1 .63g), <strong>[1003043-55-7]2-ethoxypyrimidine-5-boronic acid</strong> (778mg), Pd(PPh3)2CI2 (152mg), 1 M Na2C03 (12mL) in MeCN (12mL) was vigorously stirred at 80C under argon overnight. The reaction mixture was allowed to cool down to RT, diluted with H20 and extracted with DCM (3x). The combined org. layers were dried over MgS04, filtrated off and evaporated to dryness. The crude was purified by CC (Biotage, SNAP 50g cartridge, solvent A: Hep; solvent B: EA; gradient in %B: 10 for 5CV, 10 to 30 over 5CV, 30 for 3CV) to afford 1.35g as pale yellow resin. LC-MS (B): tR = 1 .04min; [M+H]+: 473.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.7% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 72.0℃; for 1.0h; | To a solution of 8-bromo-9-(4-[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxy}phenyl)-6,7-dihydro-5H-benzo[7]annulen-3-ol (D4) (74.9 mg, 162.69 mumol), in dioxane (1 ml) and water (0.5 ml), was added <strong>[1003043-55-7]2-ethoxypyrimidin-5-yl boronic acid</strong> (30.06 mg, 178.96 mumol), Cs2CO3(106.12 mg, 325.38 mumol), and Pd(dppf)Cl2 (7.97 mg, 9.76 mumol). The reaction mixture was heated at 72 C. for 1 hour, partitioned between water and DCM and phases separated on hydrophobic partition column. The organic solvents were concentrated under reduced pressure and the residue was purified by column chromatography eluting with a gradient of MeOH in DCM (0% to 10%) to give a solid which was further purified on strong cation exchange (SCX) column to give 47.3 mg (57.7%) of 6-(2-ethoxypyrimidin-5-yl)-5-[4-[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7H-benzo[7]annulen-2-01. |
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