Water → HCID 86671373, compound

Participants

Reaction Steps

To a solution of 5-amino-1-chloroisoquinoline (1.00 g, 5.60 mmol) in acetonitrile (25 mL) at room temperature was added pyridine (0.14 mL, 1.7 mmol) followed by phenyl chloroformate (0.70 mL, 5.6 mmol). After 15 minutes, Example 1E (0.903 g, 5.60 mmol) and N,N-diisopropylethylamine (3.9 mL, 22.4 mmol) were added and stirring continued for 15 minutes, followed by the addition of water. The solid was collected by filtration, washed with water then ether, and dried in a vacuum oven at 50° C. to provide the title compound (1.53 g, 75%). 1H NMR (300 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.46-8.28 (m, 2H), 8.03-7.86 (m, 2H), 7.73 (t, J=8.1 Hz, 1H), 7.38-7.09 (m, 5H), 6.82 (d, J=7.2 Hz, 1H), 4.16 (dd, J=13.7, 6.8 Hz, 1H), 3.20-2.98 (m, 1H), 2.44 (dd, J=12.9, 6.6 Hz, 1H), 2.19-1.93 (m, 2H), 1.86-1.59 (m, 2H), 1.59-1.39 (m, 1H). MS (DCI/NH3) m/z 366 [M+H]+.

Provenance & Evidence