Phosphoric Acid → HCID 49779328, compound

Participants

Reaction Steps

To a solution of 3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]octanenitrile (from step 3, 4.50 g, 0.0146 mol) in isopropyl alcohol (80 mL, 1 mol) was added a mixture of phosphoric acid (1.43 g, 0.0146 mol) in isopropanol (5.0 mL) while solution was kept at 60° C. The phosphoric acid salt precipitated. The heating was continued but did not affect dissolution. After being cooled to room temperature, the phosphoric acid salts were filtered off, air dried, then rinsed with some diethyl ether, and air dried. MS calculated for the base, C17H21N6(M+H)+: m/z=309.183. Found: 309.3. 1H NMR (400 MHz, DMSO-d6) δ 12.10 (1H, s), 8.79 (1H, s), 8.66 (1H, s), 8.36 (1H, s), 7.58 (1H, d, J=3.6 Hz), 6.97 (1H, d, J=3.6 Hz), 4.71 (1H, m), 3.17 (2H, m), 1.94 (1H, m), 1.81 (1H, m), 1.18 (5H, m), 0.97 (1H, m), 0.78 (3H, t, J=6.8 Hz). The product was confirmed to be 99.9% pure by three different runs on reverse phase HPLC column, and having 99.7% enantiomeric excess by six different runs on chiral HPLC column.

Provenance & Evidence