Triethylamine → HCID 11684682, compound

Participants

Reaction Steps

2-({2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}amino)ethanol (prepared as described in Example 36/30 mg, 0.07 mmol) and triethylamine (10 μl) were dissolved in DMA (0.7 ml) and chloroacetic anhydride (12 mg, 0.07 mmol) was added at −15° C. The temperature was slowly raised to room temperature and the reaction mixture was stirred for 1 hour. Sodium hydride (60%, 16 mg) was then added and the reaction mixture was stirred for 1 hour. Water was then added and the mixture evaporated and purified by preparative HPLC (column beta-basic, Hypercil 5 □m, 21×100 mm) eluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient) to give the title compound (8 mg, 24%); NMR Spectrum: 3.49 (t, 2H), 3.80-3.84 (m, 4H), 4.04 (s, 2H), 4.46 (t, 2H), 5.28 (s, 2H), 7.24 (d, 1H), 7.36 (t, 1H), 7.58 (d, 1H), 7.76 (dd, 1H), 7.88 (t, 2H), 8.12 (d, 1H), 8.19 (s, 1H), 8.32 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 496 (MH+).

Provenance & Evidence