Ammonium Chloride → 4-[(3-Fluoro-4-methylphenyl)amino]-5-methylthiothiophene-2-carboxamidine

Participants

Reaction Steps

4-[(3-Fluoro-4-methylphenyl)amino -5-methylthiothiophene-2-carboxamidine: The same procedure as in Example 253, step (b) was followed using 103 mg (0.349 mmol) of methyl 4-[(3-fluoro-4-methylphenyl)amino]-5-methylthiothiophene-2-carboxylate (as prepared in previous step), 2 mL of trimethylaluminum (2.0 M in toluene, 4 mmol), 216 mg of ammonium chloride (4 mmol) and 2 mL of toluene, and purified on a 2-g silica SPE column with 5% MeOH-CH2Cl2 to afford 45 mg (44%) of the title compound as a yellow foam 1H-NMR (DMSO-d6; 400 MHz) δ 2.13 (s, 3H), 2.50 (s, 3H ), 6.70 (m, 2H), 7.10 (m, 1H), 7.98 (s, 1H), 8.09 (s, 1H), 9.16 (br s, 4H). Mass spectrum (ESI, m/z): Calcd. for C13H14FN3S2, 296.1 (M+H), found 296.2.

Provenance & Evidence