Piperidine → HCID 178488454, compound

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 30 by employing 7-methoxy-2-(1-pyrrolidinylvinyl)benzo [b]furan (freshly prepared before use from 2-acetyl-7-methoxybenzo [b]furan (Avocado Chemical Company), pyrrolidine and TiCl4 (1.89 g, 7.77 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.61 g, 7.77 mmol), N,N-diisopropylethylamine (1.4 mL, 7.77 mmol), piperidine (1.2 mL, 12.4 mmol), NEt3 (1.7 mL) and SnCl2 (23 mL of a 2 M soln in DMF). In this example the SnCl2 solution was added to the reaction mixture at 140° C. The mixture was stirred at 140° C. for an additional 16 h then the heating was discontinued and the mixture was allowed to cool to room temperature. The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 0.27 g (10%) of 7-methoxy-2-[2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl]benzo[b]furan as a brown colored powder. This compound (0.26 g, 0.72 mmol) was dissolved in 5:1 EtOAc/MeOH (30 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (0.80 mL, 0.80 mmol). The solution was allowed to cool to room temperature. The resulting crystals were collected by filtration, washed with EtOAc (2×10 mL), Et2O (3×15 mL) and dried under vacuum at 60° C. to give 195 mg (7%) of the title compound as a yellow colored powder. Mp: >280° C. 1H NMR (DMSO-d6; 400 MHz): δ 6 1.66 (br s, 6), 2.51 (s, 3), 3.92 (s, 3), 4.01 (br s, 4), 6.88 (s, 1), 6.98 (d, 1, J=9.6), 7.20 (t, 1, J=7.8), 7.28 (d, 1, J=7.7), 7.72 (s, 1), 12.31 (s, 1), 14.09 (s, 1). MS m/z: 363 (M+1 for free base). Anal. Calcd for C21H22N4O2.HCl.0.3H2O: C, 62.38; H, 5.88; N, 13.86; Cl, 8.77. Found: C, 62.31; H, 5.81; N, 13.60; Cl, 8.82.

Provenance & Evidence