p-Toluenesulfonic acid → HCID 59447963, compound

Participants

Reaction Steps

20 mg (0.045 mmol) of 4-[2-(tert-butoxycarbonylamino-methyl)-morpholin-4-yl]-9H-pyrimido[4,5-b]indole-7-carboxylic acid methyl ester (from Synthesis 3-1-F) was dissolved in methanol and deprotected on a MP-TsOH cartridge. The product was eluted with 2 N ammonia in methanol and concentrated in vacuo to give 11.6 mg (0.034 mmol, 75%) of the title compound as a beige solid. LC-MS (1) Rt 1.68 min; m/z (ES+) 342. 1H NMR (ppm, MeOD) δ 8.41 (1H, d, J=0.8 Hz), 8.08 (1H, s), 7.88 (1H, dd, J=8.5, 1.5 Hz), 7.80 (1H, d, J=8.3 Hz), 4.21 (1H, d, J=12.6 Hz), 4.13 (1H, d, J=13.1 Hz), 4.06 (1H, dd, J=11.6, 2.5 Hz), 3.93 (3H, s), 3.81 (1H, td, J=11.9, 2.0 Hz), 3.71-3.69 (1H, m), 3.34 (2H, d, J=0.8 Hz), 3.00 (1H, dd, J=12.6, 10.8 Hz), 2.77 (1H, s), 2.76 (1H, d, J=2.5 Hz).

Provenance & Evidence