Methylamine → HCID 86679019, compound

Participants

Reaction Steps

To a THF solution (9 mL) of the intermediate from Step A above (116 mg, 0.202 mmol) was added a 2 M methanol solution of methylamine (0.809 mL, 1.619 mmol) and the resultant mixture heated at 140° C. under microwave irradiation for 1 hour. Purification by silica gel column chromatography using DCM/MeOH (with 0.5% NH4OH) gradient provided the title compound. Chiral separation using SFC on a Chiralcel OD column provided both enantiomers of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 11.52 (1H, s), 8.90-8.86 (1H, m), 8.66-8.64 (1H, m), 7.42 (1H, dd, J=8.08, 4.49 Hz), 6.77 (1H, d, J=5.11 Hz), 4.90 (2H, t, J=6.81 Hz), 3.05-2.92 (5H, m), 1.86 (3H, s). 1H NMR δ (ppm) (DMSO-d6 with added D2O): 8.86 (1H, d, J=8.14 Hz), 8.60 (1H, d, J=4.35 Hz), 7.40 (1H, dd, J=8.09, 4.54 Hz), 4.88 (2H, t, J=6.46 Hz), 2.99-2.85 (5H, m), 2.45 (3H, s), 1.81 (3H, s). m/z=524.1 (M+H).

Provenance & Evidence