1-Pyrrolidinepropanamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[3-(1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (25 mg, 0.070 mmol) described in example 92 and [3-(1-pyrrolidinyl)propyl]amine (0.08 mL of a 4.68 M solution in chloroform, 0.0364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[3-(1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (18 mg, 60% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.32 (br s, 1 H), 8.56 (s, 1 H), 8.51 (s, 1 H), 7.40 (s, 1 H), 7.17-7.14 (m, 2 H), 7.04-7.00 (m, 2 H), 4.13 (s, 2 H), 3.58 (s, 2 H), 3.54-3.52 (m, 2 H), 3.13 (br s, 4 H), 3.03-2.98 (m, 2 H), 2.19-2.06 (m, 2 H), 2.01 (br s, 4 H); HRMS m/z calcd for C24H28N4O3F: 439.2145 Found: 439.2141.

Provenance & Evidence