ChemicalBook CAS DataBase List Tacedinaline

Tacedinaline synthesis

7synthesis methods

Product Name:Tacedinaline
CAS Number:112522-64-2
Molecular formula:C15H15N3O2
Molecular Weight:269.3

Carbamic acid, N-[2-[[4-(acetylamino)benzoyl]amino]phenyl]-, 1,1-dimethylethyl ester

1299346-13-6

112522-64-2

GENERAL STEPS: Trifluoroacetic acid (22 mL) was added slowly and dropwise to a solution of tert-butyl (2-(4-acetylaminobenzoyl)phenyl)carbamate 1.5 (3.5 g, 9.5 mmol) in anhydrous dichloromethane (55 mL) at 0 °C. The reaction mixture was slowly warmed to 23 °C and stirred at this temperature for 2 h until the reaction was complete. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was diluted with water and the pH was adjusted with saturated aqueous sodium bicarbonate to about 8. The precipitate precipitated was filtered, washed sequentially with water and ether, and finally dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid in a yield of 2.4 g (96% yield).1H NMR (500 MHz, 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]+.

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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Yield: 92%

Reaction Conditions:

with sodium hydrogencarbonate in ethanol;water; pH=8 for 1.5 h;

Steps:

15
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, 92% yield, 97.0% 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).

References:

THE BROAD INSTITUTE, INC.;HOLSON, Edward;WAGNER, Florence;STAHLY, G., Patrick WO2012/3413, 2012, A1 Location in patent:Page/Page column 52-53

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References