HCID 507868, compound → HCID 59067903, compound

Participants

Reaction Steps

A suspension of 3-[2-(4-Benzoyl-piperazin-1-yl)-2-oxo-acetyl]-4-fluoro-1H-indole-7-carboxylic acid methylamide (A″′, 0.260 g., 0.60 mmol) in absolute ethanol (5 mL) under nitrogen atmosphere was treated with sodium borohydride (0.031 g, 0.8 mmol). The suspension became a solution within several minutes. The reaction was stirred overnight. Solvent was removed in-vaccuo and the residue was purified by silica gel column chromatography, eluting with ethyl acetate:methanol (100:0 changing to 90:10). Product fractions were pooled and dried in-vaccuo to give the title compound (Example 32, 0.106 g, 0.24 mmol, Y 40%). 1H—NMR (300 MHz, d-6 DMSO): 11.33 (s, 1H indole NH); 8.51 (d, 1H, CONH); 7.7-7.1 (m, 7H, aromatic); 6.85 (m, 1H, C5-H); 5.70 (b, 1H, OH); 5.27 (d, 1H, CHCO); 3.8-3.3 (2×br, 8H, piperazine)2.83 (d, 3H, CH3). LRMS (ES+) m/z [M+Na]+=460.9, (ES−) [M−H]−=437.0.

Provenance & Evidence