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CAS No. : | 1346808-41-0 | MDL No. : | MFCD17677234 |
Formula : | C10H16BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VWYZENWRLMNXDO-UHFFFAOYSA-N |
M.W : | 209.05 | Pubchem ID : | 71303784 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.7 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.95 |
TPSA : | 44.49 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) : | -6.33 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.76 |
Log Po/w (WLOGP) : | 1.28 |
Log Po/w (MLOGP) : | 0.3 |
Log Po/w (SILICOS-IT) : | 1.2 |
Consensus Log Po/w : | 0.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.43 |
Solubility : | 0.785 mg/ml ; 0.00375 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.31 |
Solubility : | 1.02 mg/ml ; 0.00488 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.23 |
Solubility : | 0.123 mg/ml ; 0.000587 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.29 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
81% | Stage #1: 4-iodo-5-methyl-1,2-oxazole With copper(l) iodide; sodium hydride; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: bis(pinacol)diborane In tetrahydrofuran at 20℃; for 1h; | 139 Example 139 6-(5-Methyl-4-isoxazolyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylo-pyranoside A solution of 0.208 g (1 mM) of 4-iodo-5-methylisoxazole in 5 ml of THF is prepared under an argon atmosphere and 0.019 g (0.1 mM) of cuprous iodide and 0.060 g (1.5 mM) of 60% sodium hydride in oil are added. The reaction mixture is stirred at ambient temperature for 5 minutes and 0.192 g (1.5 mM) of bis(pinacolato)diborane is added. The reaction mixture is subsequently stirred at ambient temperature for 1 hour, then 4 ml of a saturated sodium bicarbonate solution are added and extraction is carried out with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The pinacol ester of 5-methyl-4-isoxazoleboronic acid [1H NMR (250 MHz; d6-DMSO) δ=8.44 (s, 1H), 2.55 (s, 3H), 12.27 (s, 12H)] is obtained in the form of a white solid with a yield of 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 5h; Inert atmosphere; | U.201 Preparation of 1-benzyl-2-methyl-6H-(5-methylisoxazol-4-yl)-1H-benzo[d]imidazol-4-amine (Example Compound 201} To a solution of 82 (100 mg, 0.29 mmoi) in 1,4-dioxane (5 mL) was added 5- methylisoxazoe-4-boronic acid pinacol ester (91 mg, 0.43 mmoi), sodium carbonate (80 mg, 0.58 mmol), water (1 mL), and tetrakis(triphenylphosphine)paiadium(0) (17 mg, 0.01 mmoi). The reaction mixture was purged with nitrogen and heated at 90 °C for 5 h. The mixture was diluted with methylene chloride (70 mL), washed with brine (25 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (silica gel, 0-5% ethyl acetate/methylene chloride) to a yellow solid which was dissolved in THF (4 ml), a solution of sodium dithionite (159 mg, 0,91 rnmol) in water (2 mL) was added and the mixture was stirred at room temperature for 2 h. 2. N HCl il mL) was added to the mixture, and the mixture was'heated to reflux for 15 min. The mixture was basified by saturated aqueous sodium bicarbonate solution, and extracted with methylene chloride (40 mL χ 2). The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography (silica gel, 0-8% methanol/methylene chloride) and triturated with ethyl acetate/hexanes to afford Example Compound 201 (12 mg, 25%) as an off-white solid: H-f N M R (300 M Hz, DMSO-cf6) δ 8.69 (d, J = 0.6 Hz, 1H), 7.36-7.26 (m, 3H), 7.15 (d, J = 6.9 Hz, 2H), 6.78 (d, J = 1.5 Hz, 1H), 6.47 (d, J = 1.5 Hz, 1H), 5.40 (s, 2H), 5.33 (s, 2H), 2.50 (s, 3H), 2.47 (s, 3H); ESI m/z 319 [M + H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.1 g | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 20 - 90℃; for 1h; Microwave irradiation; | 48.d A solution of tert-butyl 3-(1-((6-bromobenzo[djthiazol-2-yl)amino)ethyl)pyrrolidine-1-carboxylate (0.1 5g, 0.352 mmol), 5 -methyl-4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)isoxazole(0.29 g, 1.41 mmol) and NaHCO3 (0.148 g, 1.76 mmol) in DMF:water (4:1; 5 ml) was stirred at rt ina microwaveable vial. The mixture was degassed for 30 mm before addition of Pd(dppf)C12 (0.025 g,0.035 mmol) and the reaction mixture was heated to 90°C for 1 h in a microwave. The resultingreaction mixture was poured into water (100 ml) and extracted with EtOAc (2 x 50 ml). The combined organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure.The cmde material was purified by flash chromatography (30% EtOAc in hexane) yielding tert-butyl3 -(1 -((6-(5 -methylisoxazol-4-yl)benzo [d jthiazol-2-yl)amino)ethyl)pyrrolidine- 1 -carboxylate (0.1 g,0.233 mmol). LCMS: Method A, 4.95 mm, MS: ES+ 429.10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate In 1,2-dimethoxyethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.8% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; |
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