Methanesulfonyl chloride → HCID 57979842, compound

Participants

Reaction Steps

3-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-N-methylpiperidine-3-carboxamide (Example 89.1, Isomer 1) (100 mg, 0.21 mmol) was dissolved in dichloromethane (2.5 ml) and diisopropylethylamine (54 μl, 0.31 mmol) added. Methanesulfonyl chloride (19 μl, 0.25 mmol) was added and the mixture stirred for 1 hour, absorbed onto an Isolute SCX column, washed with methanol and eluted with ammonia in methanol. The appropriate fractions were concentrated and the residues purified by column chromatography on silica, eluting with methanol/dichloromethane (2/98) to give the title product (Isomer 1) (70 mg, 60%) as a white solid; 1H NMR Spectrum: (DMSO d6) 1.67 (m, 1H); 1.92 (m, 2H); 2.07 (m, 1H); 2.21 (s, 3H); 2.66 (d, 3H); 2.88 (s, 3H); 3.03 (m, 1H); 3.21 (m, 1H); 3.34 (d, 1H); 3.52 (d, 1H); 3.62 (d, 1H); 3.79 (d, 1H); 3.96 (s, 3H); 7.20 (s, 1H); 7.30 (dt, 1H); 7.50 (m, 1H); 7.62 (m, 2H); 8.32 (s, 1H); 8.44 (s, 1H); 9.57 (s, 1H). Mass Spectrum: (M+H)+ 565.5

Provenance & Evidence