Tetrafluoro-m-phenylenediamine dihydrochloride → 1-(9-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)-4-(2-(pyridin-2-yl)ethyl)piperazin-2-one dihydrochloride

Participants

Reaction Steps

tert-Butyl 9-methyl-7-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (180 mg, 0.368 mmol) was deprotected and converted to the dihydrochloride salt according to Example 2 (step g) to provide the title compound (162 mg, 95%) as an off-white solid: 265° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 12.8-12.0 (br s, 1H), 9.76 (s, 2H), 8.68 (d, J=4.9 Hz, 1H), 8.12-8.06 (m, 1H), 7.69-7.64 (m, 1H), 7.59-7.55 (m, 1H), 7.52 (d, J=8.3 Hz, 1H), 7.42 (d, J=1.6 Hz, 1H), 7.01-7.00 (dd, J=8.3, 1.7 Hz, 1H), 4.44 (s, 2H), 4.07 (s, 2H), 4.05-4.01 (m, 2H), 3.78-3.72 (m, 2H), 3.71-3.62 (m, 5H), 3.51-3.45 (m, 2H), 3.47-3.43 (m, 2H), 2.95 (t, J=5.7 Hz, 2H); ESI MS m/z 390 [M+H]+; HPLC (Method B) 99% (AUC), tR=7.9 min.

Provenance & Evidence