Formaldehyde → HCID 66711266, compound

Participants

Reaction Steps

Following a procedure analogous to Example 45, 4-(3-Methoxy-4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (2.9 g) was converted to 4-(3-Methoxy-4-nitro-phenoxy)-piperidine as the trifluoroacetic acid salt (3.0 grams) which was converted, using a procedure analogous to 232a, with formaldehyde to 4-(3-Methoxy-4-nitro-phenoxy)-1-methyl-piperidine (76%), which was converted to 2-Methoxy-4-(1-methyl-piperidin-4-yloxy)-phenylamine (100%) using a procedure analogous to 251b, which was converted, using a 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (100 mg, 0.36 mmol), to the title compound (27 mgs, 16%). H-NMR (CDCl3) δ 8.70 (s, 1H), 8.25 (d, J=10.7 Hz, 1H), 8.03 (d, J=10.7 Hz, 1H), 7.44 (t, J=9.2 Hz, 1H), 7.30 (s, 1H), 7.16-7.02 (m, 3H), 6.85-96.82 (m, 1H), 6.53 (s, 1H), 6.42 (d, J=10.4 Hz, 1H), 4.27 (Broad s, 1H), 3.89 (s, 3H), 3.86 (s, 3H), 2.75-2.69 (m, 2H), 2.33 (s, 3H), 2.33-2.26 (m, 2H), 2.04-1.98 (m, 2H), 1.90-1.81 (m, 2H); LC/MS (ESI+): 460 (M+H).

Provenance & Evidence