Acetic Acid → HCID 59837534, compound

Participants

Reaction Conditions

Reaction Steps

N-[(dimethylamino)methylene]-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxamide (0.34 g, 0.88 mmol), methyl hydrazine (0.116 mL, 2.19 mmol) and acetic acid (1 mL) were combined and heated at 100° C. for 2 hours. The reaction mixture was diluted with water (10 mL), solid sodium carbonate was added until the mixture was pH9. Dichloromethane (2×50 mL) was used to extract. The combined organics were dried over sodium sulphate, filtered and concentrated in vacuo to provide a yellow oil. This was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 to 90:10:1) to produce the title compound (0.065 g, 20%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.83-1.93 (m, 4H), 2.05-2.16 (m, 2H), 2.30 (m, 2H), 2.48 (m, 2H), 2.60-2.85 (m, 6H), 3.37 (s, 3H), 3.80 (m, 2H), 3.90 (m, 2H), 4.0 (t, 2H), 6.85 (d, 2H), 7.07 (d, 2H), 7.88 (s, 1H). HRMS ESI+ m/z 371.2434 [MH]+.

Provenance & Evidence