Diisopropylethylamine → Ammonia methanol

Participants

Reaction Steps

In a 10 mL sealed tube, to 7-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (90.58 mg, 0.376 mmol) and N,N-Diisopropylethylamine (0.262 mL, 1.50 mmol) in 2.0 mL of anhydrous DMF was added N-Phenylbis(trifluoromethane)sulfonamide) (211.1 mg, 0.591 mmol). After stirring at room temperature for 2 hours, 4-(4-Amino-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.376 mmol) (synthesized according to literature procedure, Tet. Lett. 2008, 49, 2996) was added. The reaction mixture was heated at 65° C. overnight. The reaction was conc. in vacuo. The reaction mixture was purified via silica gel column chromatography using 100:1 DCM:MeOH then 500:15:10 DCM:MeOH:7N NH3/MeOH to afford the title compound as an orange foam. MP 95-100° C. LCMS (E/I+) 490.19 (M+H). 1H NMR (DMSO-d6)-9.32 (s, 1H), 8.88 (s, 1H), 7.72 (d, 1H, J=7.32 Hz), 7.69 (s, 1H), 7.48 (t, 1H, J=7.78 Hz), 7.36 (s, 1H), 7.20 (d, 1H, J=8.32 Hz), 7.11 (t, 1H, J=7.44 Hz), 6.88 (d, 1H, J=4.60 Hz), 6.85 (d, 1H, J=4.60 Hz), 4.22-4.11 (m, 1H), 4.11-3.98 (m, 2H), 3.76 (s, 3H), 3.00-2.76 (m, 2H), 1.93-1.84 (m, 2H), 1.58-1.49 (m, 2H), 1.47 (9H).

Provenance & Evidence