Ethyl isocyanatoacetate → Trifluoroacetate

Participants

Reaction Steps

A solution of 4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-N-(piperidin-4-ylmethyl)pyrimidin-2-amine hydrochloride (77 mg, 0.2 mmol), N,N-diisopropylethylamine (174 μL, 1.0 mmol) in N,N-dimethylformamide (2 mL) was treated with ethyl 2-isocyanatoacetate (23 mg, 0.2 mmol) and stirred at room temperature. Upon reaction completion the product was isolated by High Performance Liquid Chromatography using acetonitrile/water/trifluoroacetic acid as eluent. The pure product containing fractions were concentrated under reduced pressure to afford ethyl 2-(4-((4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-ylamino)methyl)piperidine-1-carboxamido)acetate as a trifluoroacetate salt. M.p.=170-172° C.; 1H NMR 400 MHz (DMSO-d6) δ 8.51 (s, 1H), 8.25 (m, 1H), 8.18 (m, 1H), 8.10 (d, J=6.3 Hz, 1H), 7.18 (m, 2H), 7.03 (d, J=7.0 Hz, 1H), 6.75 (s, 1H), 4.29 (m, 2H), 4.07 (q, J=7.0 Hz, 2H), 3.96 (d, J=10.3 Hz, 2H), 3.71 (s, 2H), 3.42 (s, 2H), 2.98 (t, J=5.9 Hz, 2H), 2.70 (t, J=11.7 Hz, 2H), 2.18 (m, 2H), 1.92 (m, 1H), 1.76 (d, J=10.2 Hz, 2H), 1.18 (t, J=7.0 Hz, 3H), 1.17 (m, 2H); LCMS: 477 [M+H].

Provenance & Evidence