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CAS No. : | 217314-47-1 | MDL No. : | MFCD09263221 |
Formula : | C9H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OWMZQNZFHGAVCN-UHFFFAOYSA-N |
M.W : | 181.19 | Pubchem ID : | 11830046 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.62 |
TPSA : | 61.55 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.36 cm/s |
Log Po/w (iLOGP) : | 1.86 |
Log Po/w (XLOGP3) : | 1.47 |
Log Po/w (WLOGP) : | 1.07 |
Log Po/w (MLOGP) : | 1.06 |
Log Po/w (SILICOS-IT) : | 0.99 |
Consensus Log Po/w : | 1.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.03 |
Solubility : | 1.68 mg/ml ; 0.00927 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.37 |
Solubility : | 0.774 mg/ml ; 0.00427 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 1.04 mg/ml ; 0.00573 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.72 |
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 |
---|---|---|
73% | With ammonium formate In methanol | Methyl 3-methoxy-5-aminobenzoate (2): 2 g (9.5 mmol) methyl 3-methoxy-5-nitrobenzoate (7) were dissolved in 50 mL methanol by heating, then 0.3 g Pd/C (10percent) were added under a stream of nitrogen, followed by 2.99 g (47.5 mmol) ammonium formate. The mixture was refluxed for 3 h, then stirred overnight at r.t.. The clear layer above the catalyst was decanted off portionwise and filtered through a syringe filter. The catalyst that remained in the flask was washed twice with methanol during this procedure. After concentration, 1.69 g of a brown solid were obtained, which were purified by column chromatography (hexanes/ethyl acetate, 7:3). Drying under vacuum afforded 1.25 g (73percent) of a colorless solid. 1H NMR (CDCl3) δ7.00-6.97 (m, 2H), 6.42 (t, J1=2.2 Hz, J2=2.2 Hz), 3.89 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 3.78 (sb, 2H); 13C NMR (CDCl3) δ167.13 160.71, 147.49, 131.95, 109.01, 105.71, 104.36, 55.19, 51.880.box.ESI-MS m/z 314 [MH]+. |
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) |
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