Isoamylamine → 2-{4-[(3-Methylbutylamino)methyl]phenoxy}thiazole-5-carboxamide

Participants

Reaction Steps

Place 2-(4-formylphenoxy)thiazole-5-carboxamide (0.187 g, 0.755 mmol), isoamylamine (0.072 g, 0.831 mmol) and 3 Å molecular sieves in a vial. Add methanol (3.8 mL), cap and stir overnight. Add NaBH4 (0.029 g, 0.755 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 5% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes to give the title compound: TOF MS ES+ 320.1 (M+H)+, HRMS calcd for C16H22N3O2S 320.1432 (M+H)+, found 320.1428, time 0.32 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min. 20-95% over 18], tR=9.7 min, 96.9% purity.

Provenance & Evidence