Formaldehyde → HCID 57979820, compound

Participants

Reaction Conditions

Reaction Steps

3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)amino]piperidin-2-one (160 mg, 0.37 mmol prepared as described in Example 10), para-formaldehyde (112 mg, 3.72 mmol) and magnesium sulfate (90 mg, 0.74 mmol) were stirred in methanol (15 ml) and sodium cyanoborohydride (94 mg, 1.49 mmol) added. The mixture was heated at 50° C. for 1.5 hours, cooled, filtered and concentrated under reduced pressure. The resulting material was purified by flash chromatography on silica, eluting with increasingly polar mixtures of methanol/methylene chloride (2/98 to 5/95) to give the title product (101 mg, 61%) as a white solid; 1H NMR spectrum: (DMSO d6) 1.77 (m, 3H), 2.02 (m, 1H), 2.40 (s, 3H), 3.09 (m, 2H), 3.29 (dd, 1H), 3.95 (s, 5H), 7.18 (s, 1H), 7.28 (t, 1H), 7.40 (brs, 1H), 7.48 (t, 1H), 7.55 (m, 1H), 8.35 (s, 1H), 8.42 (s, 1H), 9.76 (s, 1H); Mass Spectrum: (M+H)+ 444.

Provenance & Evidence