Diisopropylethylamine → HCID 86706480, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3,5-dichlorophenylamino)-1-(4-amino-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (0.2 g, 0.6 mmol) in DMF was added 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (0.17 g, 0.57 mmol) and DIEA (0.11 g, 0.85 mmol). The reaction mixture was stirred at 90° C. overnight, the mixture was diluted with EtOAc (100 mL) and washed with water (20 mL×3). The EtOAc layer was concentrated in vacuo to give a mixture which was purified by column chromatography (silica gel, gradient EtOAc in Hexanes) to give (0.160 g, 57%) of the titled intermediate. 1H NMR (CDCl3, 400 MHz): δ 8.41 (s, 1H), 8.08 (s, 1H), 8.06 (s, 1H), 8.01 (s, 1H), 7.54 (d, 1H, J=3.6 Hz), 7.33-7.19 (m, 6H), 6.83-6.67 (m, 3H), 6.35 (s, 2H), 5.35-5.25 (m, 1H), 5.18 (d, J=16.4 Hz, 1H), 4.76 (d, J=16.4 Hz, 1H), 4.51 (dd, J=1.8, 16 Hz, 1H), 4.33 (t, J=1.8 Hz, 1H), 3.82 (dd, J=1.8, 10 Hz, 1H), 3.72 (d, J=5.2 Hz, 1H), 2.38 (s, 3H). LCMS: M/z: (M+1):621

Provenance & Evidence