N,N-dimethylpiperidine-4-carboxamide → HCID 59605908, compound

Participants

Reaction Steps

A solution of 9-methyl-2-(2-methylbenzoimidazol-1-yl)-6-morpholin-4-yl-9H-purine-8-carbaldehyde (100 mg, 0.27 mmol) and piperidine-4-carboxylic acid dimethylamide (50 mg, 0.32 mmol) in DCE (3 mL) was stirred at ambient temperature for 90 min. Sodium triacetoxyborohydride (86 mg, 0.41 mmol) was added and the mixture stirred for 18 h, then loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2 M NH3 in MeOH. The product was collected and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, DCM:MeOH; 100:0, 95:5, 90:10, to 85:15) to afford 326 as a white solid (69 mg, 51%). LCMS (Method G): RT=5.48 min, M+H+=518. 1H NMR (CDCl3, 400 MHz) δ 8.19 (m, 1 H); 7.73-7.68 (m, 1 H); 7.29-7.25 (m, 2 H); 4.35 (m, 4 H); 3.91-3.83 (m, 7 H); 3.75 (s, 2 H); 3.06 (s, 3 H); 2.95 (s, 6 H); 2.54 (m, 1 H); 2.18 (m, 2 H); 1.92-1.79 (m, 2 H) and 1.71 (m, 4 H)

Provenance & Evidence