Isobutyryl chloride → HCID 11720881, compound

Participants

Reaction Steps

To a solution of 1-(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-(3-chloro-4-fluoro-phenyl)-1-[3-(4-methyl-piperazin-1-yl)-propyl]-urea (Preparative Example 27, 0.020 g, 0.042 mmol) in CH2Cl2 (0.2 mL) at 0° C. were added isobutyryl chloride (0.0054 mL, 0.052 mmol) and DIEA (0.026 mL, 0.15 mmol). After stirring from 0° C. to room temperature for 16 hours, the mixture was concentrated in vacuo and the residue was purified by preparative HPLC to give 0.020 g (88%) of N-(7-{3-(3-chloro-4-fluoro-phenyl)-1-[3-(4-methyl-piperazin-1-yl)-propyl]-ureido}-5,6,7,8-tetrahydro-naphthalen-2-yl)-isobuty ramide as a light yellow gum. 1H NMR (300 MHz, CD3OD): δ 7.60 (dd, 1H, J=6.9, 2.4 Hz), 7.40 (d, 1H, J=2.1 Hz), 7.30 (ddd, 1H, J=9.0, 4.2, 2.4 Hz), 7.20 (dd, 1H, J=8.4, 2.1 Hz), 7.15 (t, 1H, J=9.0 Hz), 7.05 (d, 1H, J=8.4 Hz), 4.31 (m, 1H), 3.62 (m, 8H), 3.49 (m, 2H), 3.27 (t, 2H, J=6.9 Hz), 2.98 (m, 7H), 2.10 (m, 4H), 1.38 (dd, 1H, J=6.6, 2.7 Hz), 1.19 (d, 6H, J=6.6 Hz). MS-ESI: 544.1 (M+H+).

Provenance & Evidence