Sulfuryl chloride → 3-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-(methylsulfonyl)azetidine-3-carboxamide

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Reaction Steps

Diisopropylethylamine (72 μl, 0.41 mmol) then sulfonyl chloride (11 μl, 0.14 mmol) were added to a solution of the hydrochloride salt of 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]azetidine-3-carboxamide (Example 74) (60 mg, 0.12 mmol) in CH2Cl2 (1 ml) at 0° C. After 1 hour, the reaction mixture was diluted in 50 ml CH2Cl2 and washed with water. The organic layer was dried on MgSO4, then concentrated under reduced pressure. The crude product was purified on preparative HPLC (standard basic condition) to give the title product (20 mg, 33%) as a white powder; 1H NMR Spectrum: (CDCl3) 2.17 (s, 3H), 3.05 (s, 3H), 3.61 (s, 2H), 3.97 (s, 3H), 4.03 (d, 2H), 4.11 (s, 2H), 7.21 (s, 1H), 7.30 (m, 1H), 7.48 (m, 2H), 7.60 (brs, 2H), 8.38 (s, 1H), 8.44 (s, 1H), 9.75 (s, 1H); Mass Spectrum: (M+H)+ 523.

Provenance & Evidence