Glycolic Acid → HCID 59605362, compound

Participants

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-8-(4-methoxypiperidin-4-yl)-9-methyl-6-morpholin-4-yl-9H-purine (150 mg, 0.32 mmol), hydroxyacetic acid (36 mg, 0.47 mmol), HOBt (47 mg, 0.35 mmol), NMM (77 μL, 0.69 mmol) and EDCI (91 mg, 0.47 mmol) in THF (3 mL) was allowed to stir at r.t. for 4 h. The resulting mixture was diluted with DCM and washed with sat. aq. NaHCO3, dried (phase separator) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, THF:EtOAc, 0-50%) then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording 823 (88 mg, 52%). LCMS (method I): RT 3.25 min, [M+H]+ 535.3. 1H NMR (DMSO, 400 MHz): δ 8.05-8.04 (1 H, m), 7.64-7.63 (1 H, m), 7.26-7.25 (2 H, m), 4.54 (1 H, t, J=5.40 Hz), 4.17-4.06 (6 H, m), 3.92 (3 H, s), 3.78 (4 H, t, J=4.51 Hz), 3.65-3.55 (1 H, m), 3.40-3.25 (3 H, m), 3.18 (1 H, m), 3.09 (3 H, s), 2.17-2.14 (4 H, m), 1.35 (3 H, t, J=7.43 Hz)

Provenance & Evidence