Ammonia → HCID 178496189, compound

Participants

Reaction Steps

A solution of Compound (7) (371.2 mg, 1.03 mmol) in a 1:1 p-dioxane:TFA (“trifluoroacetic acid”) mixture, and a catalytic amount of water was heated to 65° C. for 24 hrs. Evaporation of the solvent showed that a trifluoroacetyl adduct had formed. The adduct was converted to the desired diol by stirring in a saturated ammonia in methanol solution. Evaporation of the methanol gave Compound (8) (757.3 mg, 213%) as a white solid. (The large excess in recovery is most likely due to the presence of salts remaining in the mixture.) 1H NMR (300 MHz, DMSO) δ 3.26 (s, 3H), 3.57 (t, J=4.8, 9.3 Hz), 4.25 (t, J=4.8, 9.6 Hz, 2H), 4.43 (d, J=5.1, 2H), 7.32 (m, 4H). LCMS: m/z for C16H19N5O4++H observed 346.1 at 1.69 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Provenance & Evidence