Trifluoroacetic acid → HCID 58529458, compound

Participants

Reaction Steps

To a solution of 2-{4-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-piperidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (73.5 mg, 0.1 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.2 mL). The reaction was stirred at rt for 5 h. The sample was concentrated and the residue taken up in 1.5 mL of methanol, 0.5 mL of acetonitrile and 0.5 mL of water. The sample was then free-based using Phenomenex's Strata-X-C cation mixed mode polymer SPE plate (500 mg/6 mL/well) to give 9.20 mg (17%) of desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1 H), 7.80 (d, J=8.56 Hz, 1 H), 7.60 (s, 1 H), 7.29-7.39 (m, 5 H), 7.15 (d, J=8.56 Hz, 1 H), 6.63 (d, J=11.49 Hz, 1 H), 4.52 (d, J=12.59 Hz, 1 H), 4.05 (d, J=11.62 Hz, 1 H), 2.78 (t, J=12.47 Hz, 1 H), 2.56-2.66 (m, 1 H), 2.17 (s, 1 H), 1.99-2.10 (m, 5 H), 1.77-1.85 (m, 5 H), 1.63-1.69 (m, 2 H), 1.52-1.62 (m, 3 H), 1.17-1.27 (m, 2 H); MS LC-MS [M+H]+=521.5, RT=2.96 min.

Provenance & Evidence