Ethyl bromoacetate → HCID 68862385, compound

Participants

Reaction Steps

To a solution of 5-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(4-piperazin-1-yl-tetrahydro-pyran-4-yl)-phenyl]-amide trifluoroacetic acid salt (22 mg, 0.036 mmol) (prepared in Example 1, step (h)) in DCM (0.3 mL) was added NEt3 (0.015 mL, 0.11 mmol) and ethyl bromoacetate (0.0044 mL, 0.040 mmol) and the mixture stirred for 10 h at RT. The mixture was concentrated and the residue dissolved in 1 mL of EtOH and 7N KOH (0.031 mL, 0.22 mmol) was added and the mixture stirred for 3 h at RT. The mixture was diluted with 5 mL of H2O, the pH adjusted to 2, and the title compound purified by RP-HPLC on a C18 column eluting with a linear gradient of 20-50% CH3CN in 0.1% TFA/H2O over 10 min to give 22 mg (91%) of a white solid. 1H-NMR (400 MHz, CD3OD): δ 8.41 (d, J=8.6 Hz, 1H), 8.01 (s, 1H), 7.44 (dd, J=8.6, 2.2 Hz, 1H), 7.31 (d, J=2.2 Hz, 1H), 5.81 (m, 1H), 4.00-3.92 (m, 2H), 3.70 (s, 2H), 3.42-3.34 (m, 2H), 3.26-2.86 (m, 8H), 2.70-2.58 (m, 2H), 2.38-2.29 (m, 2H), 2.23-2.05 (m, 4H), 1.60 (t, J=6.3 Hz, 2H), 1.10 (s, 6H). Mass spectrum (APCI, m/z): Calcd. for C30H38N6O4, 545.3 (M−H). found 545.3.

Provenance & Evidence