Triethylamine → HCID 69225680, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 29D (29 mg, 0.12 mmol) in ethanol (0.5 mL) was added triethylamine (0.12 mL, 0.82 mmol), piperazine-1-carboxylic acid tert-butyl ester (33 mg, 0.18 mmol) and the mixture heated at 90° C. for 16 hours. The mixture was diluted with CH2Cl2 (25 mL) and washed with 1 M NaOH (10 mL). The layers were separated and the aqueous was extracted with CH2Cl2 (25 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of CH2Cl2:EtOAc (5:1, 2:1 and 1:1) to provide the title compound. 1H NMR (CDCl3) δ 1.49 (s, 9H), 2.72 (t, J=5.93 Hz, 2H), 3.26-3.32 (m, 4H), 3.52-3.57 (m, 4H), 4.54 (t, J=5.93 Hz, 2H), 4.78 (s, 2H), 7.09 (dd, J=8.14, 1.36 Hz, 1H), 7.17-7.24 (m, 1H), 7.35-7.42 (m, 1H), 7.89 (dd, J=7.80, 1.70 Hz, 1H).

Provenance & Evidence