Hydroxylamine → HCID 75628450, compound

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine (16.3 M solution in water, 0.33 mL, 5.21 mmol) was added to 2-(3,5-dimethylisothiazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile (18 mg, 0.05 mmol) in MeOH (2 mL) and the reaction was stirred at 130° C. for 20 min in the microwave. The mixture was purified by preparative HPLC to give E24 2-(3,5-dimethylisothiazol-4-yl)-N′-hydroxy-3-(4-hydroxyphenyl)-1H-indole-1-carboximidamide (7.0 mg, 35%); ES/MS m/z 379.11 (M+H), 377.14 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.70 (dd, 1H, J=7.9, 1.0 Hz), 7.59 (dd, 1H, J=9.0, 0.9 Hz), 7.29 (m, 1H), 7.20 (m, 1H), 7.09 (m, 2H), 6.81 (m, 2H), 2.30 (s, 3H) and 2.16 (s, 3H) and E25 2-(3,5-dimethylisothiazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide (5 mg, 26%), ES/MS m/z 364.11 (M+H), 362.14 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.12 (d, 1H, J=8.4 Hz), 7.67 (d, 1H, J=7.9 Hz), 7.36 (m, 1H), 7.26 (m, 1H), 7.05 (m, 2H), 6.83 (m, 2H) and 2.21 (s, 6H). For each of the title compounds, identification by 1H-NMR showed that the amide oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained.

Provenance & Evidence