Propanal → HCID 11960632, compound

Participants

Reaction Steps

A solution of the free base of Example 10E (70 mg, 0.3 mmol) in methanol (5 mL) was treated with propionaldehyde (25 mg, 0.4 mmol) at room temperature overnight. Sodium triacetoxyborohydride (254 mg, 1.2 mmol) was then added and the solution was stirred at rt for 3 h. After concentration under vacuum, the residue was separated by HPLC (Zorbax C-8, 0.1% TFA/CH3CN/H2O) to give 55 mg of desired product. Yield: 35%. MS (APCI) m/z 287 (M+H)+; 1H NMR (500 MHz, CD3O): δ 0.89 (t, J=7.33 Hz, 2 H), 1.60 (s, 3 H), 1.63-1.77 (m, 2 H), 2.12-2.40 (m, 1 H), 2.59-2.73 (m, 1 H), 3.03-3.40 (m, 5 H), 3.69 (s, 1 H), 3.96-4.50 (m, 1 H), 7.21 (t, 1 H), 7.56 (s, 1 H), 7.76 (s, 1 H); Anal. Calcd for C16H22N4O.2.0 TFA: C, 46.70; H, 4.70; N, 10.89. Found: C, 46.89; H, 4.68; N, 10.98.

Provenance & Evidence