Water → 3-[2-(3-Trifluoromethyl-phenoxy)-ethylamino]-pyrrolidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-amino-pyrrolidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (300 mg, 0.74 mmol) in N,N-dimethylformamide (5 mL) was treated with N,N-diisopropylethylamine (285 mg, 2.20 mmol) and 1-(2-bromoethoxy)-3-(trifluoromethyl) benzene (220 mg, 0.81 mmol). The reaction mixture was allowed to stir at 80° C. for 1 h. At this time, the reaction was poured into water. The aqueous layer was extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Preparative high pressure liquid chromatography afforded 3-[2-(3-trifluoromethyl-phenoxy)-ethylamino]-pyrrolidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (28 mg, 8%) as a light brown solid; LRMS for C20H21F3N6O3S (M+H)+ at m/z=482. The NMR spectrum obtained on the sample is compatible with its structure.

Provenance & Evidence