ChemicalBook CAS DataBase List TAK-063

TAK-063 synthesis

5synthesis methods

Product Name:TAK-063
CAS Number:1238697-26-1
Molecular formula:C23H17FN6O2
Molecular Weight:428.42

288-13-1
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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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1238697-26-1
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Yield: 44%

Reaction Conditions:

with copper(I) oxide;salicylaldehyde-oxime;caesium carbonate in acetonitrile for 5 h;Reflux;Inert atmosphere;

Steps:

120
Example 1201-[2-Fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one A suspension of 1-(2-fluoro-4-iodophenyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (4.88 g, 10 mmol), pyrazole (0.681 g, 10 mmol), Cu₂O (0.143 g, 1 mmol), salicylaldoxime (0.549 g, 4 mmol), and Cs₂CO₃(6.52 g, 20 mmol) in CH₃CN (100 mL) was refluxed for 5 h under Ar atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO₄, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography eluting with hexane/THF (1/2) and recrystallized from EtOH/H₂O to give the title compound (1.90 g, 44% yield) as a pale yellow powder: mp 214-216° C.; ¹H NMR (300 MHz, CDCl₃) δ ppm 3.92 (3H, s), 6.44 (1H, t, J=9.0 Hz), 6.53 (1H, dd, J=1.9, 2.3 Hz), 7.30 (1H, ddd, J=1.1, 2.3, 9.0 Hz), 7.34 (1H, d, J=1.9 Hz), 7.37-7.48 (5H, m), 7.61 (1H, dd, J=2.3, 12.4 Hz), 7.76 (1H, d, J=1.9 Hz), 7.79 (1H, d, J=1.9 Hz), 7.82 (1H, d, J=2.3 Hz), 7.92 (1H, d, J=2.3 Hz). LC-MS (ESI) m/z 429 [M+H]⁺. Anal. Calcd for C₂₃H₁₇FN₆O₂: C, 64.48; H, 4.00; N, 19.62. Found: C, 64.41; H, 4.00; N, 19.54.

References:

Taniguchi, Takahiko;Kawada, Akira;Kondo, Mitsuyo;Quinn, John F.;Kunitomo, Jun;Yoshikawa, Masato;Fushimi, Makoto US2010/197651, 2010, A1 Location in patent:Page/Page column 139

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100-63-0 Synthesis