Diisopropylethylamine → HCID 69087553, compound

Participants

Reaction Steps

In a round bottom flask, 5-{(1R)-2-[(±)-2,5-diazabicyclo[4.1.0]hept-2-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one TFA salt (66 mg, 0.126 mmol) was dissolved in DMF (2 mL). DIEA (66 mg, 0.511 mmol) was added, followed by [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid (32 mg, 0.153 mmol). HATU (73 mg, 0.192 mmol) was added and let reaction stir at room temperature for 6 hours. Then reaction was diluted by adding small amount of water and was put on prep-HPLC for purification (Sunfire-C18 column, eluted by 10-75% AcCN/H2O+0.1% formic acid). Lyophilization gave the title compound. 1H NMR (ppm) (500 MHz, CD3OD): δ 9.90 (1H, s), 8.50 (1H, s), 8.07-8.00 (2H, m), 7.80 (1H, m), 7.72 (1H, d, J=8.0 Hz), 5.36 (2H, d, J=3.10 Hz), 5.40-5.31 (1H, m), 4.10 (2H, s), 4.08-3.95 (1H, m), 3.20-3.07 (1H, in), 3.06-2.83 (3H, m), 2.80 (2H, s), 2.78-2.68 (2H, m), 2.54-2.39 (1H, m), 2.36 (3H, s), 0.95 (1H, t, J=6.39 Hz), 0.81 (1H, t, J=4.98 Hz); LC/MS: (M+23)+ =498.

Provenance & Evidence