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CAS No. : | 218594-15-1 | MDL No. : | MFCD07363808 |
Formula : | C10H13BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LSFAQGJWQMNXLP-UHFFFAOYSA-N |
M.W : | 273.13 | Pubchem ID : | 7204889 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 62.18 |
TPSA : | 51.22 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 2.54 |
Log Po/w (XLOGP3) : | 2.44 |
Log Po/w (WLOGP) : | 3.0 |
Log Po/w (MLOGP) : | 1.54 |
Log Po/w (SILICOS-IT) : | 1.82 |
Consensus Log Po/w : | 2.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.216 mg/ml ; 0.00079 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.16 |
Solubility : | 0.189 mg/ml ; 0.000694 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.83 |
Solubility : | 0.0406 mg/ml ; 0.000149 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.56 |
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 |
---|---|---|
91% | With triethylamine In dichloromethane at 20℃; for 4 h; | To a solution of 6- bromopyridin-3 -amine (5.4 g, 28.9 mmol) in dichloromethane (200 mL) were added triethylamine (4.4 g, 43.3 mmol) and di-tert-butyl dicarbonate (7.6 g, 34.7 mmol). The resulting solution was stirred for 4 hours at ambient temperature and quenched with water (300 mL). The organic layer was separated and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with 2-10percent ethyl acetate in petroleum ether to afford tert-butyl (6- bromopyridin-3-yl)carbamate as a colorless solid: MS (ESI, m/z): 273.1, 275.1 [M + 1]+; 1H MR (300 MHz, OMSO-d6) δ 9.72 (s, 1H), 8.45 (d, J= 1.8 Hz, 1H), 7.83 (d, J= 5.4 Hz, 1H), 7.53 (d, J= 5.7 Hz, 1H), 1.48 (s, 9H). |
25% | With triethylamine In dichloromethane at 0 - 20℃; for 16 h; | To a stirred solution of 6-bromopyridin-3-amine (5 g, 28.90 mmol) and TEA (8.75 g, 86.70 mmol) in DCM (50ml) was added Boc20 (12.6 g, 57.80 mmol) at 0°C and stirred for 16 hat RT. The reaction mixture was dilutedwith DCM washed with water. The organic layer was dried over anhydrous Na2S04 and concentrated underreduced pressure. The obtained crude compound was purified by flash column chromatography using 20percentEtOAc in petroleum ether as eluent to obtain the title compound (2.0 g, 25percent) as white solid. LC-MS (method 2): Rt = 2.65 min; m/z = 275.17 (M+H++2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.0833333 h; Stage #2: at 20℃; for 0.5 h; Stage #3: With hydrogenchloride In tetrahydrofuran; water |
To a solution of 3-amino-6-bromopyridine (8.65 g, 50 mmol) in THF (100 mL) at 0° C. was added sodium bis(trimethylsilyl)amide (1 M solution in THF, 105 mL, 105 mmol). After addition, the reaction was stirred at 0° C. for 5 min, and then di-tert-butyl dicarbonate (12 g, 55 mmol) was added in several portions. After addition, the reaction was stirred at RT for 30 min, and then diluted with water (60 mL) and neutralized by adding ice-cold 1N HCl (about 90 mL) to pH=78. The resultant mixture was extracted with EtOAc (3.x.100 mL). The combined organics were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (330 g) column chromatography eluting with a gradient of EtOAc (0-50percent) in hexane to give the title compound as an off-white solid (11.6 g, 85percent). LC/MS (method A): retention time=3.47 min, (M+H-tBu))+=217. |
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