Diisopropylethylamine → HCID 67209217, compound

Participants

Reaction Steps

To the solution of 5-methoxy-indan-1-ylamine hydrochloride (92 mg, 0.46 mmol) and (3-cyclopropyl-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (building block A7, 120 mg, 0.46 mmol) in DMF (6 ml) were added DIPEA (0.24 ml, 1.38 mmol) and HATU (210 mg, 0.55 mmol) and the reaction was stirred at it for 30 min. The mixture was diluted with EtOAc, washed with aqueous bicarbonate solution and brine, dried over sodium sulfate, and the solvents were evaporated under reduced pressure. Purification by preparative HPLC (Gilson GX-281, Waters Sunfire C18, 5 μm, 30×100 mm with guard column 19×10 mm, solvent A: water with 0.1% TFA, solvent B: acetonitrile, gradient 40-60% B in 15 min, flow reate 50 ml/min) gave the title compound as colorless solid (140 mg, 75%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.40 (d, 1H), 7.02 (d, 1H), 6.81 (s, 1H), 6.68 (d, 1H), 6.48 (s, 1H), 5.26 (dd, 1H), 4.80 (s, 2H), 3.76 (s, 3H), 3.71 (s, 3H), 2.91-2.88 (m, 1H), 2.78-2.73 (m, 1H), 2.66 (s, 3H), 2.38-2.33 (m, 1H), 2.28-2.24 (m, 1H), 1.89-1.82 (m, 1H), 0.92-0.85 (m, 4H); LCMS RtH=3.095 min; [M+H]+=407.2]

Provenance & Evidence