Methylamine → HCID 18428682, compound

Participants

Reaction Steps

The product from example 158 (480 mg, 1.51 mmol) WSCDI (377 mg, 2 mmol), HOBt.H2) (255 mg, 1.66 mmol) and triethylamine (0.53 mL, 3.78 mmol) were dissolved in DCM (0.03 M). After stirring for 30 min, MeNH2 (condensed, 2 mL) was added and the mixture stirred for a further 12 h. The mixture was then evaporated and the residue partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (3 times). The combined organic layers were dried (MgSO4) and evaporated to a yellow oil, which was purified by flash chromatography [SiO2; DCM/ MeOH/ 880 NH3 (93:7:1)]. The desired title amide was isolated as its hydrochloride salt (285 mg, 63%); Free base: δH(CDCI3, 400 MHz) 2.12 (6 H, s), 2.41 (3 H, s), 2.92 (3 H, d), 3.46 (3 H, s), 6.78 (1 H, brd), 6.84 (2 H, d), 7.20 (2 H, d), 7.63 (1 H, dd), 7.82 (1 H, d); MS m/z (ES+) 331 (MH+)

Provenance & Evidence