tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-butyl 7-{[6-(2-chlorophenyl)-5-oxo-5,6-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-2-yl]amino}-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Steps

A mixture of Example 1E (0.900 g, 2.501 mmol) and tert-butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.994 g, 4.00 mmol) was heated in a capped vial at 90° C. for 1 hour. The reaction mixture were suspended and stirred in ethyl acetate. The solids were filtered and washed with ethyl acetate. The filter cake was stirred in saturated aqueous NaHCO3, filtered, washed with water, and oven-dried to provide the title compound. The filtrate was diluted with ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over MgSO4, filtered, concentrated, and purified on an 80 g column using the ISCO Companion flash system eluting with CH2Cl2/ethyl acetate (6:4 to 5:5) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.44 (s, 9H), 2.77 (t, J=5.75 Hz, 2H), 3.58 (t, J=5.75 Hz, 2H), 4.54 (s, 2H), 7.07 (d, J=1.59 Hz, 1H), 7.21 (d, J=8.72 Hz, 1H), 7.53-7.66 (m, 5H), 7.69-7.74 (m, 1H), 7.76 (d, J=1.59 Hz, 1H), 9.12 (s, 1H), 10.71 (s, 1H). MS (ESI+) m/z 544.1 (M+H)+.

Provenance & Evidence