Pivaloyl chloride → 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 pivaloyl chloride (24 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 1-(4-((4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-ylamino)methyl)piperidin-1-yl)-2,2-dimethylpropan-1-one as a trifluoroacetate salt. M.p.=170-172° C.; 1H NMR 400 MHz (DMSO-d6) δ 8.47 (s, 1H), 8.19 (m, 1H), 8.09 (d, J=6.3 Hz, 1H), 7.98 (m, 1H), 7.15 (m, 2H), 7.03 (d, J=7.0 Hz, 1H), 4.28 (m, 4H), 2.98 (t, J=5.9 Hz, 2H), 2.78 (t, J=12.1 Hz, 2H), 2.18 (m, 2H), 1.99 (m, 1H), 1.81 (d, J=11.7 Hz, 2H), 1.19 (s, 9H), 1.14 (m, 2H); LCMS: 432 [M+H].

Provenance & Evidence