4-Chlorobenzenesulfonyl 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 4-chlorobenzene-1-sulfonyl chloride (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 N-((1-(4-chlorophenylsulfonyl)piperidin-4-yl)methyl)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-amine as a trifluoroacetate salt. M.p.=140-142° C.; 1H NMR 400 MHz (DMSO-d6) δ 8.53 (s, 1H), 8.27 (s, 1H), 8.13 (s, 1H), 8.08 (d, J=6.7 Hz, 2H), 7.73 (d, J=9.0 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H), 7.17 (m, 2H), 7.04 (d, J=7.0 Hz, 1H), 4.29 (m, 2H), 3.68 (d, J=12.1 Hz, 2H), 3.41 (s, 2H), 2.97 (t, J=5.9 Hz, 2H), 2.33 (t, J=11.7 Hz, 2H), 2.18 (m, 2H), 1.95 (d, J=12.9 Hz, 2H), 1.75 (m, 1H), 1.31 (m, 2H); LCMS: 522 [M+H].

Provenance & Evidence