Diisopropylethylamine → HCID 66711064, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-(2,3-Dihydro-benzofuran-7-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (0.100 g, 0.395 mmol, 1.05 eqv) and N,N-Diisopropylethylamine (0.28 mL, 4.22 eqv) in anhydrous DMF (1 mL) in a 10 mL sealed tube was added N-Phenylbis(trifluoromethane-sulfonimide (0.148 g, 1.105 eqv.). The mixture was stirred at room temperature for 1 h and to it (R)-1-(7-amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-ol (0.094 mg, 0.38 mmol, 1.00 eqv.) was added. The reaction mixture was heated at 70° C. for 2 h, concentrated in vacuo and purified via prepTLC (silica gel; eluant: 6% methanol in methylene chloride) to afford (R)-1-{7-[7-(2,3-Dihydro-benzofuran-7-yl)-pyrrolo[2,1-f]triazin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-propan-2-ol as a dark brown solid (0.018 g, 10%). MP>200° C. (decomp.). LCMS (E/I+) 486.16 (M+H). 1H NMR (CDCl3) δ 8.80 (s, 1H), 8.30 (d, 2H, J=6.50 Hz), 7.45 (s, 1H), 7.30 (s, 2H), 7.00 (dd, 1H, J=6.00H, 6.00 Hz), 6.80 (d, 1H, J=6.00 Hz), 6.65 (s, 1H), 4.80 (t, 2H, J=6.00 Hz), 3.90 (broad, 1H), 3.80 (s, 3H), 3.30 (t, 2H, J=6.00 Hz), 2.90-2.10 (overlapping m, 11H), 1.10 (d, 3H, J=6.00 Hz).

Provenance & Evidence