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CAS No. : | 14338-36-4 | MDL No. : | MFCD00075058 |
Formula : | C8H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XUSKZLBLGHBCLD-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 571807 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 42.39 |
TPSA : | 63.32 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) : | -6.51 cm/s |
Log Po/w (iLOGP) : | 0.98 |
Log Po/w (XLOGP3) : | 1.0 |
Log Po/w (WLOGP) : | 0.9 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | 0.82 |
Consensus Log Po/w : | 0.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -1.68 |
Solubility : | 3.17 mg/ml ; 0.0209 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.92 |
Solubility : | 1.82 mg/ml ; 0.0121 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.8 |
Solubility : | 2.4 mg/ml ; 0.0159 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
87% | for 2 h; Heating / reflux | (3-Amino-phenyl)-acetic acid methyl ester (3a). Thionyl chloride (4.8 mL, 66.16 mmol) was carefully added drop wise to MeOH (100 mL) at 0 0C. To the resulting solution was added a suspension of 3-amino-phenylacetic acid (5.0 g, 33.08 mmol) in MeOH (100 mL) and the reaction mixture was refluxed for 2 h. Then MeOH was distilled off and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The phases were separated and the organic phase was washed with sat. aq. NaHCO3, dried (Na2SO4) and evaporated which gave the title compound (4.77, 87percent). |
87% | Stage #1: at 0℃; for 2 h; Heating / reflux Stage #2: With water; sodium hydrogencarbonate In ethyl acetate |
(3-Amino-phenyl)-acetic acid methyl ester (40a); Thionyl chloride (4.8 mL, 66.16 mmol) was carefully added drop wise to MeOH (100 mL) at 0 0C. To the resulting solution was added a suspension of 3-amino-phenylacetic acid (5.0 g, 33.08 mmol) in MeOH (100 mL) and the reaction mixture was refluxed for 2 h. Then MeOH was distilled off and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The phases were separated and the organic phase was washed with sat. aq. NaHCO3, dried (Na2SO4) and evaporated to give 4.77 (87percent) of the title compound. |
83% | at 0℃; for 4 h; | 3-AMINOPHENYLACETIC acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 ML, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4). Methyl 3-aminophenylacetate was isolated as a brown oil. (14. 1g, 83percent). 1H NMR (500 MHz, CDC13) 8 7.12 (1H, dd), 6.7-6. 6 (3H, m), 3.71 (3H, s), 3.55 (2H, s). Methyl (3-Methanesulfonylamino-phenyl)-acetate : Methyl 3-aminophenylacetate |
83% | Stage #1: at 0℃; for 4 h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
Methyl 3-aminophenylacetate:; 3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2S04). Methyl 3-aminophenylacetate was isolated as a brown oil. (14.1g, 83percent). 1H NMR (500 MHz, CDC13) 8 7.12 (1H, dd), 6.7 - 6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s). |
83% | at 0℃; for 4 h; | Methyl 3-aminophenylacetate: 3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 ML) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4). Methyl 3-aminophenylacetate was isolated as a brown oil. (14. 1g, 83percent).APOS;H NMR (500 MHz, CDCL3) 8 7.12 (1H, dd), 6.7- 6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s). |
83% | at 0℃; for 4 h; | Example 15; 3-(Methanesulfonylamino)phenylacetic acid:; Step A: 3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise while stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4) to afford methyl 3-aminophenylacetate as a brown oil. (14.1g, 83percent). 1H NMR (CDCl3) No. 7.12 (1H, dd), 6.7 - 6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s). |
77% | for 18 h; Heating / reflux | Example 6; a) (3-f [5-(2-Methoxy-phenyl)-furan-2-carbonyl]-amino}- phenyl)-acetic acid (17); (i) (3-Amino-phenyl)-acetic acid methyl ester (15); 3-Aminophenylacetic acid (5 g, 33.1 mmol) was esterified with MeOH using Method B to give the title compound Yield: 4.22 g, 77percent; LC/MS tr 0.70 min; MS (ES+) m/z 166 (M+H); A solution of carboxylic acid (1 eq) was heated under reflux for 18 h with H2SO4 (0.5 vol) in MeOH or EtOH (25 vol). The solvent was evaporated in vacuo and the residue partitioned between DCM and aqueous sodium bicarbonate. The DCM layer was washed with brine, dried (Na2SO4), filtered and the solvent removed in vacuo to give the ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sulfuric acid In methanol for 48 h; Heating / reflux | Step 1: Dissolve (3-Amino-phenyl)-acetic acid ((24),700mg, 4.63mmol) in MeOH (21mL) and add conc. sulfuric acid (0.27mL, 5.09mmol). Stir the reaction mixture for 2d under reflux. Cooled mixture to room temperature (rt), remove solvent under reduced pressure and prepurify the residue by flushing it over a short pad of silica gel using EtOAc. Remove solvent again and partitione the residue between EtOAc and saturated aqu. NaHCO3 (1+1). Extracte the aqueous layer 3 times with EtOAc, washe the combined organic layers with brine and dried with Na2SO4. Remove solvent under reduced pressure and dry the residue without further purification in oil pump vacuum to obtain product (25) as a light yellow oil (708mg, 92percent). 1H NMR (400MHz, CDCl3): 3.51 (s, 2 H); 3.67 (s, 3 H); 6.57 (dd, 1 H, J1 = 7.8Hz, J2 = 1.BHz); 6.60 (br.Ψt, 1 H, J = 1.8Hz); 6.65 (br.d, 1 H, J 7.8Hz); 7.08 (Ψt, 1 H, J = 7.8Hz). |
92% | With sulfuric acid In methanol at 20℃; for 48 h; Heating / reflux | Dissolve (3-Amino-phenyl)-acetic acid ((22),700mg, 4.63mmol) in MeOH (2 1 mL) and add conc. sulfuric acid (0.27mL, 5.09mmol). Stir the reaction mixture for 2d under reflux. Cooled mixture to room temperature (rt), remove solvent under reduced pressure and prepurify the residue by flushing it over a short pad of silica gel using EtOAc. Remove solvent again and partition the residue between EtOAc and saturated aqu. NaHCO3 (1+1). Extracte the aqueous layer 3 times with EtOAc, washe the combined organic layers with brine and dried with Na2SO4. Remove solvent under reduced pressure and dry the residue without further purification in oil pump vacuum to obtain product (23) as a light yellow oil (708mg, 92percent). 1H NMR (400MHz, CDCl3): 3.51 (s, 2 H); 3.67 (s, 3 H); 6.57 (dd, 1 H, J1 = 7.8Hz, J2 = 1.8Hz); 6.60 (br.Ψt, 1 H, J= 1.8Hz); 6.65 (br.d, 1 H, J 7.8Hz); 7.08 (Ψt, 1 H, J= 7.8Hz). |
79% | With HCl conc.; sodium hydrogencarbonate In methanol; hexane; ethyl acetate | Methyl-3-aminophenylacetate (1) To a solution of 3-aminophenylacetic acid (3 g, 19.85 mmol) in methanol (50 mL) at room temperature was added HCl conc. (37percent, 7.5 mL). The mixture was stirred 6 h at room temperature then treated with a saturated aqueous solution of NaHCO3. The solvent was removed under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) and evaporated. The crude mixture was purified by flash chromatography using hexane/AcOEt (1:1) yielding 1 as a yellow oil (3.06 g, 79percent). 1H NMR: (300 MHz, CDCl3): 7.10 (t, J=8 Hz, 1H), 6.68-6.58 (m, 3H), 3.69-3.65 (m, 5H), 3.53 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | for 3 h; Heating / reflux | Example 4: Synthesis of 4- { [ (5-Phenyl-furan-2-carbonyl)- amino]-methyl}-benzoic acid (10); (a) Ethyl-3-aminophenyl acetate (6); A stirred solution of 3-aminophenyl acetic acid (1 g, 6.6 mmoles) (5) and conc. sulphuric acid (2 ml) in ethanol (20 ml) was refluxed for 3 hours. The solvent was evaporated and the residue dissolved in ethyl acetate, washed with water, sodium carbonate, brine, water, and finally dried (MgSO4). After concentrating in vacuo (6) (918mg) was obtained as dark red oil.; aa) (3-[5-(4-Fluoro-phenyl)-furan-2-carbonyl]-amino3- phenyl)-acetic acid (42); (i) Altermate sytnehsis of (3-Amino-phenyl)-acetic acid ethyl ester (6); 3-Aminophenylacetic acid (2 g, 13 mmol) was esterified with EtOH using Method B to give the title compound. Yield: 2.1 g, 89percent ; LC/MS tr 0.78 min; MS (ES+) m/z 180 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.8% | With thionyl chloride In methanol | A. 3-Amino phenylacetic acid methylester hydrochloride A suspension of 3-amino phenylacetic acid (5.0 g, 33 mmol) in methanol (50 ml) at 0° C. under argon was slowly treated with thionyl chloride (19.4 g, 165 mmol). After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 16 hours. The solvent was evaporated and the residue was triturated with ethyl ether to give 3-amino phenylacetic acid methylester hydrochloride (5.3 g, 96.8percent) as a colorless solid. 1 H NMR (CDCl3) δ 10.6 (s, 2 H), 7.42 (m, 4 H), 3.68 (s, 3 H). 3.66 (s,2 H); 13 C NMR (CDCl3) 172.5, 137.3, 133.1, 131.2, 130.8, 125.9, 123.7, 53.5, 41.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: With sodium carbonate In 1,4-dioxane; waterCooling with ice Stage #2: at 20℃; for 4 h; |
A solution of 3-aminophenylacetic acid (12, 4g, 26.46 mmol, 1 equiv.) in a mixture of dioxane (52 mL) and water (52 mL), and sodium carbonate(2.8 g, 26.42 mmol, 1 equiv., in 26 mL of water) was stirred and cooled in an ice bath. Di-tert-butyldicarbonate (BOC-anhydride, 6.24 g, 28.59 mmol, 1.1 equiv.) was added in one portion, and stirringwas continued at room temperature for 4 h. The dioxane was removed in vacuo and the aqueouslayer chilled, covered with a layer of ethyl acetate, and acidified to pH 4 with dilute KHSO4. This wasfollowed by extraction (ethyl acetate) and purification by a filtration on silica with dichloromethanefollowed by ethyl acetate to yield the compound 13 (Scheme 8; 6.65 g; 85percent) of a white solid. 1H-NMR(300 MHz, CDCl3): 7.31 (d, 2H, J = 8.4 Hz), 7.20 (d, 2H, J = 8.4 Hz), 6.56 (br s, 1H), 3.59 (s, 2H), 1.5 (s, 9H). |
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