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CAS No. : | 74165-74-5 | MDL No. : | MFCD07783718 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DBEMTZANGFGKMX-UHFFFAOYSA-N |
M.W : | 167.16 | Pubchem ID : | 13874409 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 44.3 |
TPSA : | 72.55 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) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 1.1 |
Log Po/w (XLOGP3) : | 1.54 |
Log Po/w (WLOGP) : | 0.98 |
Log Po/w (MLOGP) : | -0.37 |
Log Po/w (SILICOS-IT) : | 0.5 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.08 |
Solubility : | 1.38 mg/ml ; 0.00823 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.67 |
Solubility : | 0.355 mg/ml ; 0.00212 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.53 |
Solubility : | 4.91 mg/ml ; 0.0294 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
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 |
---|---|---|
79% | at 0 - 20℃; for 2 h; | Thionyl chloride (26 mL; 359 mmol) was added dropwise to a solution of 3-amino-5- methoxybenzoic acid (1 Og; 59.82 mmol) in MeOH (150 mL) at 0°C. The reaction mixture was stirred for 2 hours at room temperature. The precipitate was filtered off, washed with DIPE and dried under vacuo at 50°C to give 8.6 g (79percent) of intermediate 1 19 (a white solid) . |
46 g | Stage #1: at 0 - 20℃; for 72 h; Stage #2: With sodium hydrogencarbonate In diethyl ether; dichloromethane; water |
To a stirred suspension of 3-amino-5-methoxyben- zoic acid (47 g, 281 mmol) in MeOH (1 L) at 0° C. was added thionyl chloride (123 mE, 1687 mmol) dropwise. The reaction was warmed to it and stirred for 72 h. The resulting solid was isolated by filtration, washing with diisopropyl ether, affording the product as the HC1 salt. The filtrate was evaporated, the residue triturated with MeOH/ether, filtered and washed with ether. The combined solid was suspended in DCM (500 mE) and basified with sat. aq. NaHCO3 solution (300 mE) with vigorous stirring. The organic phase was separated, washed with brine (200 mE), dried (MgSO4), filtered and evaporated under reduced pressure to give a solid. The solid was triturated with ether/isohexane to afford the sub-title compound (46 g) as a solid.‘H NMR (400 MHz, DMSO-d6) ö: 6.83 (dd, 1H),6.63 (dd, 1H), 6.37 (t, 1H), 5.42 (s, 2H), 3.79 (s, 3H), 3.70 (s, 3H). LCMS mlz 182 (M+H) (ES) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; | (3-Amino-5-methoxyphenyl)methanol (13). To a solution of 12 (5 g, 0.03 mol) in anhydrous THF (100 mL) was added LiALH4 (2.3 g, 0.06 mol) in portions at 0 °C. The reaction mixture was stirred overnight, cooled to 0 °C, and quenched by slow addition of aqueous KOH solution (20percent, 5 mL) followed by ethyl acetate (50 mL). The mixture was filtered through a pad of Celite and rinsed with ethyl acetate. The filtrate was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude was purified by flash chromatography (60:40 → 40:60, hexanes:EtOAc) to give compound 13 as a pale yellow solid (2.75 g, 60percent). 1H NMR (400 MHz, CDCl3): δ 6.38 (s, 1H), 6.34 (s, 1H), 6.31 (s, 1H), 4.39 (s, 2H), 3.79 (s, 3H), 3.77 (s, 2H). 13C NMR (100 MHz, CDCl3): δ 160.61, 147.49, 143.13, 105.90, 102.04, 99.87, 64.98, 54.78 |
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