Methylamine → HCID 59129402, compound

Participants

Reaction Conditions

Reaction Steps

1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1H-indol-5-yl)cyclopropanecarboxamide (320 mg, 0.84 mmol) was dissolved in a mixture composed of anhydrous DMF (0.5 mL) and anhydrous THF (5 mL) under N2. NaH (60% in mineral oil, 120 mg, 3.0 mmol) was added at room temperature. After 30 min of stirring, the reaction mixture was cooled to −15° C. before a solution of epichlorohydrin (79 μL, 1.0 mmol) in anhydrous DMF (1 mL) was added dropwise. The reaction mixture was stirred for 15 min at −15° C., then for 8 h at room temperature. MeNH2 (2.0 M in MeOH, 1.0 mL) was added and the mixture was heated for 10 min at 105° C. in the microwave oven. The mixture was cooled, filtered and purified by preparative HPLC to give 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(2-hydroxy-3-(methylamino)propyl)-1H-indol-5-yl)cyclopropanecarboxamide. 1 H NMR (400 MHz, DMSO-d6) δ 8.50(s, 1H), 7.60-7.59(m, 1H), 7.35(dd, J=14.3, 8.9 Hz, 1H), 7.10(d, J=8.8 Hz, 1H), 1H), 6.94(dd, J=8.0, 1.6 Hz, 1H), 6.91(d, J=7.9 Hz, 1 H), 6.20(d, J=2.3 Hz, 1H), 6.03(s, 2H), 2.82(d, J=4.7 Hz, 1H), 2.72(d, J=4.7 Hz, 1H), 2.55(dd, J=5.2, 5.2 Hz, 1H), 2.50(s, 3H), 1.43(s, 9H), 1.39(dd, J=6.4, 3.7 Hz, 2H), 1.04(dd, J=6.5, 3,9 Hz, 2H). MS (ESI) (M+H) 464.0.

Provenance & Evidence