ChemicalBook CAS DataBase List Tacedinaline

Tacedinaline synthesis

7synthesis methods

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

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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112522-64-2
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References