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CAS No. : | 112522-64-2 | MDL No. : | |
Formula : | C15H15N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAZAPHZUAVEOMC-UHFFFAOYSA-N |
M.W : | 269.30 | Pubchem ID : | 2746 |
Synonyms : |
N-acetyldinaline;CI-994;CI994, CI-994, CI 994, PD123654, PD-123654, PD 123654, Tacedinaline, acetyldinaline;Acetyldinaline;PD-123654;Goe-5549
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.07 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 79.37 |
TPSA : | 84.22 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) : | -7.06 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 1.25 |
Log Po/w (WLOGP) : | 2.11 |
Log Po/w (MLOGP) : | 1.84 |
Log Po/w (SILICOS-IT) : | 1.49 |
Consensus Log Po/w : | 1.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.41 |
Solubility : | 1.04 mg/ml ; 0.00388 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.62 |
Solubility : | 0.651 mg/ml ; 0.00242 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.94 |
Solubility : | 0.00306 mg/ml ; 0.0000114 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
96% | Stage #1: With trifluoroacetic acid In dichloromethane at 0 - 23℃; for 2 h; Stage #2: With sodium hydrogencarbonate In water |
To a 0 °C solution of tert-butyl (2-(4-acetamidobenzamido)phenyl) carbamate 1.5 (3.5 g, 9.5 mmol) in dry dichloromethane (55 mL) was added trifluoroacetic acid (22 mL) dropwise. The mixture was allowed to slowly warm to 23 °C for 2 hours until the reaction was complete. The solvents were removed in vacuo. The reaction mixture was diluted with water and the pH was adjusted to ~8 with a saturated aqueous solution of sodium bicarbonate. The resulting precipitate was filtered, washed with water and ether, and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid. Yield 1.6 = 2.4 g (96percent).1H NMR (500 Hz, d6-DMSO) δ 10.18 (s, 1H), 9.54 (s, 1H), 7.93 (d, J = 8.5Hz, 2H), 7.69 (d, J = 8.5Hz, 2H), 7.15 (d, J = 7.5Hz, 1H), 6.96 (t, J= 7.5Hz, 1H), 6.78 (d, J = 7.5Hz, 1H), 6.59 (t, J = 7.5Hz, 1H), 4.88 (s, 2H), 2.08 (s, 3H). MS (ESI+): m/z 269.9 [M+H]+. |
96% | With trifluoroacetic acid In dichloromethane at 0 - 23℃; for 2 h; | To a 0° C. solution of tert-butyl (2-(4-acetamidobenzamido)phenyl) carbamate 1.5 (3.5 g, 9.5 mmol) in dry dichloromethane (55 mL) was added trifluoroacetic acid (22 mL) dropwise. The mixture was allowed to slowly warm to 23° C. for 2 hours until the reaction was complete. The solvents were removed in vacuo. The reaction mixture was diluted with water and the pH was adjusted to 8 with a saturated aqueous solution of sodium bicarbonate. The resulting precipitate was filtered, washed with water and ether, and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid. Yield 1.6=2.4 g (96percent). 1H NMR (500 Hz, d6-DMSO) δ 10.18 (s, 1H), 9.54 (s, 1H), 7.93 (d, J=8.5 Hz, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.15 (d, J=7.5 Hz, 1H), 6.96 (t, J=7.5 Hz, 1H), 6.78 (d, J=7.5 Hz, 1H), 6.59 (t, J=7.5 Hz, 1H), 4.88 (s, 2H), 2.08 (s, 3H). MS (ESI+): m/z 269.9 [M+H]+. |
84% | With trifluoroacetic acid In dichloromethane at 0 - 23℃; | To a 0 °C solution of Boc protected benzamide 5 (18 g, 48.7mmol) in dry DCM (250 mL) was added TFA (100 mL) portion wise. The mixture was allowed to slowly warm to 23 °C. After stirring for 2 h, TLC showed that the reaction was complete. The TFA was removed in vacuo and the reaction mixture was diluted with water and the pH was adjusted to ~8 with sat. NaHCC>3. The resulting precipitate was filtered, washed with water, ether and dried under vacuum to afford 4-acetamido-N-(2- aminophenyl)benzamide 6 as an off-white solid.Yield: (11.5 g, 84percent). TLC : good, Rf = 0.3 (10percent MeOH in DCM) lU NMR (DMSO-d6, 500 MHz) δ 10.18(s, IH), 9.54 (s, IH), 7.93 (d, 2H, 7=9.0 Hz), 7.69 (d, 2H, 7=8.0 Hz), 7.15 (d, IH, 7=7.5 Hz), 6.96 (t, IH, 7=8.0 Hz), 6.78 (d, IH, 7=8.0 Hz), 6.59 (t, IH, 7=7.5 Hz), 4.87 (br s, 2H), 2.08 (s, 3H);MS: 270[M+1]+; HPLC: 97.71percent at 210nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16 h; | To the extent possible, the procedure set forth in Thomas, M. et al., Bioorganic & Medicinal Chemistry 2008, 16, 8109-8116, was followed as described herein. To a stirred solution of 4-acetamido benzoic acid 7.4 (2.5 g, 13.95 mmol, 1.0 eq.) in N,N-dimethylformamide (50 mL) was added o-phenyldiamine 7.7 (4.53 g, 41.9 mmol, 3.0 eq.), followed by N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.48 g, 18.14 mmol, 1.3 eq.) and catalytic 4-(dimethylamino)pyridine (0.18 g, 1.47 mmol, 0.1 eq.). The reaction mixture was stirred at room temperature for 16 hours. The solvents were removed under reduced pressure at 58° C. The crude residue was diluted with dichloromethane (100 mL) and kept in the refrigerator overnight. The resulting precipitate was filtered, washed with hot dichloromethane (100 mL), and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 7.6 as an off-white solid. Yield 7.6=2.48 g (66percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydrogencarbonate In ethanol; water for 1.5 h; | The dried solid of 4-acetamido-N-(2-aminophenyl)benzamide trifluoroacetate salt was suspended in a solution of 1 : 1 EtOH:H20 (320mL). Saturated NaHC03 solution (lOOmL) was added slowly to adjust the pH to 8. The resultant slurry was stirred for 1.5 hours. The precipitates were filtered and washed with water (2 X 60mL). After drying at 40°C in vacuo for 16h, 4-acetamido-N-(2-aminophenyl)benzamide (21.3g, 92percent yield, 97.0percent HPLC purity) was isolated as crystalline Form B (white solid).1HNMR (400 Hz, d6-DMSO) δ: 10.22 (s, 1H), 9.58 (s, 1H), 7.94 (d, J= 8.8 Hz, 2H), 7.70 (d, J = 8.8 Hz, 2H), 7.16 (dd, J = 1.2 Hz, 8.0 Hz, 1H), 6.97 (app dt, J= 1.6 Hz, 8.4 Hz, 1H), 6.79 (dd, J = 1.2 Hz, 8.0 Hz, 1H), 6.6 ( app dt, J= 1.6 Hz, 8.4 Hz, 2H), 4.90 (s, 2H), 2.10 (s, 3H). |