Methanesulfonyl chloride → HCID 11642491, 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 (from Preparative Example 27, 0.035 g, 0.074 mmol) in CH2Cl2 (0.2 mL) at 0° C. were added methanesulfonyl chloride (0.0058 mL, 0.074 mmol) and DIEA (0.039 mL, 0.22 mmol). The mixture was stirred from 0° C. to room temperature for 3 hours, then concentrated in vacuo, and the residue was purified by preparative HPLC to give 0.035 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)-methanesulfonamide as a light yellow gum. 1H NMR (300 MHz, CD3OD): δ 7.59 (dd, 1H, J=6.6, 2.7 Hz), 7.30 (ddd, 1H, J=9.0, 4.2, 2.7 Hz), 7.14 (t, 1H, J=9.0 Hz), 7.08 (d, 1H, J=8.4 Hz), 7.04-6.98 (m, 2H), 4.30 (m, 1H), 3.66 (m, 8H), 3.46 (m, 2H), 2.99 (m, 6H), 2.90 (s, 3H), 2.11 (m, 4H). MS-ESI: 552.0 (M+H+).

Provenance & Evidence