Ammonium Chloride → HCID 68044431, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the material from Example 4, Step 8 (98 mg, 0.128 mmol) in 1.2 mL of DMF at 0° C. were added 1-hydroxybenzotriazole (26 mg, 0.192 mmol), ammonium chloride (14 mg, 0.256 mmol), HATU (73 mg, 0.192 mmol) and N,N-diisopropylethylamine (67 μL, 0.358 mmol). The reaction mixture was stirred at 0° C. over the week-end. It was poured into water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by reverse phase column using Zorbax Eclise Plus C18 RRHT 3×50 mm, 1.8 u column. Gradient: MeCN/H2O+0.1% HCO2H from 10:90 to 95:5 over 5 minutes. Flow: 1.0 mL/min. Positive ion mode. The title compound was obtained as a colorless foam. LCMS (M+1)=764. 1H NMR (Acetone-d6): δ 9.56 (s, 1H), 8.83 (d, J=12.07 Hz, 1H), 8.41-8.25 (m, 1H), 8.08 (d, J=8.22 Hz, 1H), 7.59 (s, 1H), 7.48-7.38 (m, 4H), 7.35-7.25 (m, 4H), 7.24-7.13 (m, 2H), 6.81 (s, 1H), 6.76-6.60 (m, 1H), 6.46 (d, J=8.74 Hz, 1H), 5.16-5.02 (m, 1H), 4.49-4.41 (m, 1H), 4.38-4.31 (m, 1H), 3.69-3.57 (m, 1H), 3.34 (s, 3H), 3.47-3.20 (m, 3H), 3.14-2.89 (m, 1H), 2.71-2.26 (m, 4H), 2.04-1.84 (m, 2H), 1.52-1.10 (m, 2H).

Provenance & Evidence