ATRELEUTON synthesis

5synthesis methods

Product Name:ATRELEUTON
CAS Number:154355-75-6
Molecular formula:C16H15FN2O2S
Molecular Weight:318.37

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

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Yield: 33%

Steps:

12.B N-{3-[5-(4-Fluorophenylmethyl)-2-thienyl]-1-methyl-2-propynyl}-N-hydroxyurea
EXAMPLE 12B N-{3-[5-(4-Fluorophenylmethyl)-2-thienyl]-1-methyl-2-propynyl}-N-hydroxyurea Using the procedures described in Example 1C, the compound resulting from Example 12A (13.3 g, 49.0 mmol) was converted to the alcohol intermediate in a yield of 9.16 g (71%). In a manner analogous to the procedures described in Example 1D, the alcohol intermediate from above was converted to the title compound in 33% yield. m.p. 141°-142° C. (dec.). ¹ H NMR (DMSO-d₆, 300 MHz) δ1.32 (d, J=6.0 Hz, 3H), 4.10 (s, 2H), 5.10 (q, J=6.0 Hz, 1H), 6.50 (s, 2H), 6.80 (d, J=3.0 Hz, 1H), 7.05 (d, J=3.0 Hz, 1H), 7.13 (m, 2H), 7.28 (m, 2H), 9.30 (s, 1H). MS (DCI/NH₃) m/e 319(M+H)⁺, 336 (M+H+NH₃)⁺. Analysis calcd for C₁₆ H₁₅ FN₂ O₂ S: C, 60.36; H, 4.75; N, 8.80. Found: C, 60.53; H, 4.68; N, 8.8.

References:

Abbott Laboratories US5288751, 1994, A

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References