Water → HCID 66795949, compound

Participants

Reaction Steps

To a solution of 1.75 g (4.10 mmol) of N-[(6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridin-2-yl)methylene]-2,4,6-trimethylaniline in 20 ml of methanol, 0.42 g (6.70 mmol) of NaBH3CN was added in one portion followed by addition of three drops of 88% formic acid. The reaction mixture was refluxed under inert atmosphere for 1 hour and then poured into 50 ml of water. The crude product was extracted with 3×20 ml of ether. The organic extract was washed with water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 1.60 g (90%) of orange oil. Anal. calc. for C30H35N3: C, 82.34; H, 8.06; N, 9.60. Found: C, 82.56; H, 8.21; N, 9.59. 1H NMR (CDCl3): 7.89 (d, J=8.5 Hz, 1H, 4-H in naphthyl), 7.86 (m, 1H, 8-H in naphthyl), 7.77 (m, 1H, 4-H in Py), 7.65 (d, J=8.5 Hz, 3-H in naphthyl), 7.43 (m, 1H, 7-H in naphthyl)), 7.87 (m, 1H, 3-H in Py), 7.30-7.35 (m, 3H, 5-H in Py and 5,6-H in naphthyl), 6.80 (s, 2H, 3,5-H in mesityl), 4.35 (m, 2H, CH2NHtBu), 3.55 (m, 2H, CH2NMes), 2.94 (br. s, 2H, NH), 2.24 (s, 6H, 2,6-Me in mesityl), 2.22 (s, 3H, 4-Me in mesityl), 0.96 (s, 9H, tBu).

Provenance & Evidence