Diisopropylethylamine → HCID 178520726, compound

Participants

Reaction Steps

(S)-2-(1,4-Dichloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino [3,4-e]indazol-7-yl)acetic acid(95 mg, 0.232 mmol) was dissolved in N,N-dimethylformamide (2.0 ml). TBTU (79 mg, 0.246 mmol) was added to the mixture followed by 3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one (72 mg, 0.293 mmol) and then N,N-diisopropylethylamine (150 μl, 0.861 mmol). Reaction stirred at room temperature for 4 hours. Reaction was quenched with 50% acetonitrile-water. Material was purified by reverse phase prep HPLC (water-acetonitrile-trifluoroacetic acid). Acetonitrile was removed from the fractions by roto-vap. Remaining aqueous was made basic with aqueous sodium bicarbonate. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as white solid in 59% yield. 1H NMR (500 MHz, DMSO-D6) δ ppm 13.88 (s, 1H) 8.49 (s, 1 H) 7.35 (s, 1H) 7.00-7.09 (m, 3H) 6.70-6.87 (m, 1H) 5.42 (s, 2H) 4.49 (d, J=12.51 Hz, 1H) 4.36-4.45 (m, 1H) 4.25-4.36 (m, 1H) 4.11-4.24 (m, 1H) 3.91-4.10 (m, 2H) 3.34-3.41 (m, 2H) 3.19 (d, J=18.01 Hz, 1H) 3.05-3.15 (m, 1H) 2.93-3.03 (m, 1H) 2.83-2.93 (m, 3H) 2.53-2.65 (m, 1H) 2.32-2.47 (m, 1H) 1.57-1.87 (m, 3H) 1.44-1.57 (m, 1H). High resolution MS m/e (M+H)−=637.1735.

Provenance & Evidence