2-Methoxyethylamine → N-(3-Fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Participants

Reaction Steps

Aldehyde 141 (0.20 g, 0.362 mmol) and 2-methoxyethylamine (0.158 mL, 1.810 mmol) were dissolved in THF (50 mL) to give a colorless solution. Sodium trisacetoxyborohydride (0.384 g, 1.810 mmol) was added and the mixture was stirred at r.t. for 20 h. Additional 2-methoxyethylamine (0.158 mL, 1.810 mmol) and sodium trisacetoxyborohydride (0.384 g, 1.810 mmol) were added, and the mixture was stirred for a further 20 h. It was then concentrated, partitioned between water and dichloromethane. Organic phase was collected, washed with H2O, 1M NaOH, and brine, dried (MgSO4), filtered and concentrated. The residue was purified by Gilson Reverse Phase HPLC (Aquasil C18, 40-90% MeOH/water, 30 min, elutes 20 min) and lyophilized, to afford title compound 142. Starting material (50 mg) was also isolated.

Provenance & Evidence