Acetonitrile → Trifluoroacetate

Participants

Reaction Steps

A solution of Example 66A (180 mg, 0.48 mmol) in trifluoroacetic acid (5 mL) was heated at 50° C. for 16 h. After cooling, acetonitrile was added and the mixture concentrated on a rotary evaporator. The residue was separated by HPLC (Zorbax C-18, 0.1% TFA/CH3CN/H2O) to provide the title product as trifluoroacetate salt. This product was treated with 1.0 M solution of HCl in ether to yield the HCl salt. Yield: 92 mg (60%). MS (DCI/NH3) m/z 245 (M+H)+; 1H NMR (500 MHz, DMSO-d6): δ 0.77-0.85 (m, 2H), 0.86-0.92 (m, 2H), 2.04-2.17 (m, 1H), 3.24-3.32 (m, 2H), 3.33-3.41 (m, 2H), 3.74 (s, 3H), 3.84-3.96 (m, 2H), 5.27 (br s, 1H), 9.64 (br s, 1H). Anal. Calcd for C13H16N4O.2.1HCl: C, 48.91; H, 5.69; N, 17.46. Found: C, 48.91; H, 5.88; N, 17.11.

Provenance & Evidence