Hydrochloric Acid → HCID 58721758, compound

Participants

Reaction Steps

A suspension of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-piperidin-4-one 7A-96 (48 mg, 0.11 mmol) in methanol (0.4 ml) was cooled to 0° C. and then treated with 2-propylamine (15 μl, 0.15 mmol) and then concentrated aqueous HCl. After stirring 5 minutes, a solution of sodium cyanide (8.1 mg, 0.16 mmol) in water (0.4 ml) was added; the heterogeneous reaction was warmed to room temperature and then allowed to stir overnight. Tetrahydrofuran (0.4 ml) was then added to solubilize all reactants. Additional sodium cyanide (8 mg, 0.16 mmol) and 2-propylamine (3 drops) were added and stirred overnight. The reaction was filtered and then concentrated under reduced pressure to give title compound 22A-1 (27 mg, 48%) as a colorless solid: +ESI MS (M+1) 506.1; 1H NMR (400 MHz, CD2Cl2) δ 8.32 (s, 1H), 7.52 (d, J=7.9 Hz, 1H), 7.45–7.33 (m, 5H), 7.21 (d, J=8.7 Hz, 2H), 5.50 (v br s, 2H), 3.88 (v br s, 2H), 3.18 (septuplet, J=6.0 Hz, 1H), 2.16 (m, 2H), 1.82 (ddd, J=13.3, 10.4, 3.7 Hz, 2H), 1.16 (d, J=6.2 Hz, 6H).

Provenance & Evidence