Formaldehyde → HCID 57526732, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 13-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-[(cis-3,5-dimethyl-1-piperazinyl)carbonyl]-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxamide (42 mg, 0.066 mmol), zinc chloride (27.4 mg, 0.20 mmol), paraformaldehyde (6.0 mg, 0.20 mmol), and sodium cyanoborohydride (12.7 mg, 0.20 mmol) in MeOH was heated at 60° C. for 2 hrs. The mixture was quenched with 0.5 mL of NaOH (1N). The solution was extracted with ethyl acetate and the extract washed with dilute sodium bicarbonate (2×), brine (3×), and then dried (Na2SO4). The extract was concentrated and the crude product purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave, the titled compound as a yellow solid (35 mg, 82%). ESI-MS m/z 648 (MH+); 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 0.77-1.58 (m, 10 H) 1.69-2.19 (m, 6 H) 2.76-2.91 (m, 4 H) 3.01 (s, 6 H) 3.12-3.38 (m, 5 H) 3.91 (s, 3 H) 4.33-4.49 (m, 2 H) 5.07-5.22 (m, 1 H) 6.99 (s, 1 H) 7.08 (d, J=2.44 Hz, 1 H) 7.16 (dd, J=8.70, 2.59 Hz, 1 H) 7.56 (t, J=9.31 Hz, 2 H) 7.93 (d, J=8.55 Hz, 1 H) 8.11 (s, 1 H).

Provenance & Evidence