Diisopropylethylamine → HCID 51352570, compound

Participants

Reaction Steps

Following the same procedure in Example 31, method B, using 2,2-difluoroethylamine (138 mg, 1.7 mmol), N,N-diisopropylethylamine (0.8 ml, 4.4 mmol), HATU (646 mg, 1.7 mmol) and 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (1.1 mmol) in DMF (15 mL). The crude product was purified on LCMS using high pH column 40-70% acetonitrile gradient to afford 9 mg (2% yield) of the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.43-1.51 (m, 3 H), 1.51-1.58 (m, 2 H), 1.60 (s, 9 H), 3.22 (q, J=7.36 Hz, 1 H), 3.33 (d, J=2.93 Hz, 1 H), 3.62 (m, 1 H), 3.68-3.76 (m, 1 H), 3.90 (dd, J=10.64, 3.42 Hz, 2 H), 4.43 (d, J=7.42 Hz, 2 H), 5.90 (m, 1 H), 6.68 (dd, J=3.03, 1.46 Hz, 1 H), 7.30-7.34 (m, 1 H), 7.87 (s, 1 H), 7.90-7.99 (m, 2 H), 8.28 (s, 1 H); MS (APPI) (M+H)+=509.3.

Provenance & Evidence