Reaktion #434092

Reaktionsgleichung

1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethylamine

3-acetamido-phthalic anhydride

sodium acetate

→

N-{2-[1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide

Lösungsmittel

acetic acid

Reaktionsbedingungen

Vorschrift

N-{2-[1-(4-Difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro -1H-isoindol-4-yl}-acetamide was prepared by the procedure of example 4 from 1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethylamine (0.6 g, 0.2 mmol), 3-acetamido-phthalic anhydride (0.4 g, 0.2 mmol) and sodium acetate (0.16 g, 0.2 mmol) in acetic acid (15 ml) to give N-{2-[1-(4-difluoromethoxy-3-ethoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide as white solid (0.4 g, 40%): mp 118–120° C.; 1H NMR (CDCl3) δ1.45 (t, J=7.0 Hz, 3H, CH3), 2.27(s, 3H, CH3CO), 2.92(s, 3H, SO2CH3), 3.66 (dd, J=3.8, 14 Hz, 1H, CH2), 4.11 (q, J=6.8 Hz, 2H, OCH2), 5.88–5.94 (m, 1H, NCH), 6.55 (t, JH-F=75 Hz, 1H, CF2H), 7.12–7.16 (m, 3H, Ar), 7.49 (d, J=7.5 Hz, 1H, Ar), 7.66 (t, J=7.5 Hz, 1H, Ar), 8.77 (d, J=8.5 Hz, 1H, Ar), 9.44 (s, 1H, NH); 13C NMR (CDCl3) δ 14.5, 24.9, 41.7, 48.3, 54.1, 64.9, 11.5, 113.6, 115.0, 115.8, 118.3, 120.0, 120.2, 123.1, 125.1, 130.9, 135.4, 136.2, 137.7, 140.4, 150.9, 167.4, 169.1, 169.4; Anal Calcd for C22H22F2N2O7S: C, 53.22; H, 4.47; N, 5.64. Found: C, 53.18; H, 4.20; N, 5.64.

Quelle