1-Pyrrolidineethanamine → 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364160Notes

Reaction equation

HRID 2364160 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[N:26]1([CH2:31][CH2:32][NH2:33])[CH2:30][CH2:29][CH2:28][CH2:27]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([NH:33][CH2:32][CH2:31][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 546808827-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[2-(1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-(1-pyrrolidinyl)ethylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.61 (1H, br), 8.28 (1H, br s), 7.36 (1H, s), 7.30 (2H, m), 7.14 (2H, t, J=8.8 Hz), 4.04 (2H, s), 3.41 (2H, m), 2.56 (2H, t, J=6.4 Hz), 2.54-2.48 (4H, m), 1.68 (4H, m); ES+ MS: 411 (M+H+, 100).

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-e27ca6404e6b485ea339e367ffdb96b6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…