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CAS No. : | 111714-47-7 | MDL No. : | MFCD11656627 |
Formula : | C10H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UWOWQJXAUBYDTF-UHFFFAOYSA-N |
M.W : | 193.20 | Pubchem ID : | 10856336 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.32 |
TPSA : | 69.39 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) : | -6.53 cm/s |
Log Po/w (iLOGP) : | 1.71 |
Log Po/w (XLOGP3) : | 1.33 |
Log Po/w (WLOGP) : | 1.27 |
Log Po/w (MLOGP) : | 1.0 |
Log Po/w (SILICOS-IT) : | 1.36 |
Consensus Log Po/w : | 1.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.99 |
Solubility : | 1.95 mg/ml ; 0.0101 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.39 |
Solubility : | 0.79 mg/ml ; 0.00409 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.45 |
Solubility : | 0.679 mg/ml ; 0.00352 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.57 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
50% | With boron trifluoride diethyl etherate; In benzene; for 0.5h;Heating / reflux; | 5-Amino-furan-2-carboxylic acid methyl ester (0.42 g, 3.0 mmol) were mixed together with methyl vinyl ketone (10 ml.) in benzene and heated at reflux for 1 h. Evaporation of solvents were followed by flash chromatography using DCM / MeOH (95:5) as eluent to yield 44% (278 mg. 1.31 mmol) of 5-Acetyl-4-amino-1-hydroxy-cyclohexa-2,4-dienecarboxylic acid methyl ester. This compound were mixed with BF3 OEt2 ((284 mg, 2.0 mmol) in benzene (15 ml.) and refluxed for 0.5 h. The reaction mixture was quenched with NaHCO3 (sat) and extracted with dichloromethane. A precipitation formed in the organic phase was collected and confirmed to be the product by characterization with LC-MS and 1H NMR. Yield: 127 mg (50%). |
50% | With boron trifluoride diethyl etherate; In benzene; for 0.5h;Heating / reflux; | 4.26a 3-Acetyl-4-amino-benzoic acid methyl ester; delta-Amino-furan^-carboxylic acid methyl ester (0.42 g, 3.0 mmol) were mixed together with methyl vinyl ketone (10 ml.) in benzene and heated at reflux for 1 h. Evaporation of solvents were followed by flash chromatography using DCM / MeOH (95:5) as eluent to yield 44% (278 mg. 1.31 mmol) of 5-Acetyl-4-amino-1-hydroxy-cyclohexa-2,4-dienecarboxylic acid methyl ester. This compound were mixed with BF3 OEt2 (284 mg, 2.0 mmol) in benzene (15 ml.) and refluxed for 0.5 h. The reaction mixture was quenched with NaHCO3 (sat) and extracted with dichloromethane. The precipitation formed in the organic phase was collected and confirmed to be the product by characterization with LC-MS and 1H NMR. Yield: 127 mg (50%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine;dmap; In dichloromethane; for 1 - 16h; | 4.27 3-Acetyl-4-methanesulphonylamino-benzoic acid; Methanesulfonyl chloride was added to a solution of <strong>[111714-47-7]3-acetyl-4-amino-benzoic acid methyl ester</strong> (4.87) in dichloromethane, pyridine and a catalytic amount of DMAP. After 1-16 hrs the mixture <n="50"/>was concentrated to near dryness and the product crystallized from added ethanol. This product was hydrolyzed in 2.5 M LiOH, THF, MeOH in a microwave oven at 1 10 0C for 30 min. After cooling, the solution was acidified with aq. HCI and extracted with ethyl acetate, dried with Na2SO4 and concentrated to dryness. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 87 PREPARATION OF 1-CYCLOHEXYL-2- [3 ,4 -DIMETHOXY-4-(PYRROLIDINE-1-CARBONYL) BIPHEN-2- YLLQUINOLIN-6-YLT-LH-BENZIMIDAZOLE-S-CARBOXVLIC acid (Compound 419) Step 1: 3-ACETYL-4-IODOBENZOIC acid methyl ester (Compound 419a); [0450] A suspension of 1.45 g (7.56 mmol) of <strong>[111714-47-7]3-acetyl-4-aminobenzoic acid methyl ester</strong> in 15 mL OF 6N HCI and 3 mL MeOH was stirred and cooled to 0C. (See Padwa, A.; et al. J. Org Chem. 1997,62, 4088-4096). A solution of 0.63 g (9.07 mmol) OF NAN02 in 5 mL H20 was added dropwise to the suspension while stirring. The resulting solution was stirred at 0C for 15 min. A solution of 3.77 g of KI in 25 mL H20 was added dropwise to this solution. The flask was removed from the cooling bath and stirred overnight. The mixture was extracted with 3X50 mL EtOAc. The organic layer was washed with 10% Na2S203 solution until all 12 was removed. A pale yellow solution was obtained which was dried (NA2S04) and concentrated. The residue was purified on silica gel using hexane and EtOAc as eluent yielding 2 g yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.6% | Preparation Example F-2. 4-Oxo-1,4-dihydro-cinnoline-6-carboxylic acid methyl ester To a solution of <strong>[111714-47-7]3-acetyl-4-amino-benzoic acid methyl ester</strong> (2063mg, 10.68mmol) in acetic acid (39mL) was added sulfuric acid (6.5mL) on an ice bath, then, an aqueous solution (6.5mL) of sodium nitrite (922mg, 13.35mmol) was added thereto, followed by stirring on the ice for 1 hour, and at room temperature for 2 days. The reaction mixture was concentrated until it reached half of the amount, water was added, then an aqueous solution of 2N sodium hydroxide was added on an ice bath to adjust the pH to 5. The insoluble matter was separated by filtration, then, the filtrate was extracted with ethyl acetate, the organic layer was dried over sodium sulfate and then evaporated. Diethyl ether was added to the resulting residue for solidification, the resulting solid was washed with diethyl ether, and 365mg of the title compound (1.78mmol, 16.6%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 3.88 (3H, s), 7.66 (1H, d, J= 8.8Hz), 7.82 (1 H, s), 8.24 (1 H, d, J=8.8Hz), 8.58 (1H, s), 13.7(1 H, brs). | |
16.6% | With sodium nitrite; In sulfuric acid; water; acetic acid; at 0 - 20℃; for 49h; | To a solution of <strong>[111714-47-7]3-acetyl-4-amino-benzoic acid methyl ester</strong> (2063mg, 10.68mmol) in acetic acid (39mL) was added sulfuric acid (6.5mL) on an ice bath, then, an aqueous solution (6.5mL) of sodium nitrite (922mg, 13.35mmol) was added thereto, followed by stirring on the ice for 1 hour, and at room temperature for 2 days. The reaction mixture was concentrated until it reached half of the amount, water was added, then an aqueous solution of 2N sodium hydroxide was added on an ice bath to adjust the pH to 5. The insoluble matter was separated by filtration, then, the filtrate was extracted with ethyl acetate, the organic layer was dried over sodium sulfate and then evaporated. Diethyl ether was added to the resulting residue for solidification, the resulting solid was washed with diethyl ether, and 365mg of the title compound (1.78mmol, 16.6%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 3.88 (3H, s), 7.66 (1H, d, J= 8.8Hz), 7.82 (1 H, s), 8.24 (1 H, d, J=8.8Hz), 8.58 (1 H, s), 13.7(1 H, brs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.4% | To a solution of 4-amino-3-iodo-benzoic acid methyl ester (11.30g, 40.77mmol) in toluene (300mL) were added tributyl(1-ethoxyvinyl)tin (16.5mL, 48.9mmol) and tetrakis(triphenylphosphine)palladium(0) (9422mg, 8.154mmol) under nitrogen atmosphere, and the solution was stirred at 105C for 7 hours. After cooling to room temperature, water was added, the mixture was extracted with ethyl acetate-tetrahydrofuran, the organic layer was washed with water, and then, evaporated. The residue was dissolved in 280mL of tetrahydrofuran, 2N hydrochloric acid (80mL) was added thereto, followed by stirring for 3 hours at room temperature. The reaction mixture was cooled on an ice bath, an aqueous solution of 2N sodium hydroxide (80mL) was added, an aqueous solution of saturated sodium bicarbonate was further added, and the solution was extracted with ethyl acetate. An aqueous solution of 10% potassium fluoride was added to the organic layer, and the solution was stirred for 3 hours at room temperature. The organic layer was separated, washed with brine, then evaporated, the residue was purified by silica gel column chromatography (hexane-ethyl acetate), and title compound (6.42g, 33.2mmol, 81.4%) was obtained. 1H-NMR Spectrum (CDCl3) delta(ppm) : 2.64 (3H, s), 3.89 (3H, s), 6.63 (1H, d, J=8.8Hz), 7.91 (1 H, dd, J=2.0, 8.8Hz), 8.47 (1 H, d, J=2.0Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.4% | Preparation Example F-1. 3-Acetyl-4-amino-benzoic acid methyl ester To a solution of 4-amino-3-iodo-benzoic acid methyl ester (11.30g, 40.77mmol) in toluene (300mL) were added tributyl(1-ethoxyvinyl)tin (16.5mL, 48.9mmol) and tetrakis(triphenylphosphine)palladium(0) (9422mg, 8.154mmol) under nitrogen atmosphere, and the solution was stirred at 105C for 7 hours. After cooling to room temperature, water was added, the mixture was extracted with ethyl acetate-tetrahydrofuran, the organic layer was washed with water, and then, evaporated. The residue was dissolved in 280mL of tetrahydrofuran, 2N hydrochloric acid (80mL) was added thereto, followed by stirring for 3 hours at room temperature. The reaction mixture was cooled on an ice bath, an aqueous solution of 2N sodium hydroxide (80mL) was added, an aqueous solution of saturated sodium bicarbonate was further added, and the solution was extracted with ethyl acetate. An aqueous solution of 10% potassium fluoride was added to the organic layer, and the solution was stirred for 3 hours at room temperature. The organic layer was separated, washed with brine, then evaporated, the residue was purified by silica gel column chromatography (hexane-ethyl acetate), and title compound (6.42g, 33.2mmol, 81.4%) was obtained. 1H-NMR Spectrum (CDCl3) delta (ppm): 2.64 (3H, s), 3.89 (3H, s), 6.63 (1H, d, J=8.8Hz), 7.91 (1 H, dd, J=2.0, 8.8Hz), 8.47 (1 H, d, J=2.0Hz). |
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