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

HRID 2364191Notes

Reaction equation

HRID 2364191 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26](OCC)=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[OH:34][CH2:35][CH2:36][NH2:37]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26]([NH:37][CH2:36][CH2:35][OH:34])=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 58882907Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 588829897-[(4-Fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-hydroxyethylamine by methods similar to those described in Example 6. The product was obtained as a white solid: 1H NMR (CDCl3) δ 10.38 (1H, br m), 8.60 (1H, s), 8.07 (1H, s), 7.24 (2H, m), 7.00 (2H, t, J=8.6 Hz), 4.36 (2H, t, J=7 Hz), 4.15 (2H, s), 3.87 (2H, t, J=5 Hz), 3.66 (2H, m), 3.51 (2H, t, J=8 Hz), 3.45 (2H, t, J=7 Hz), 2.37 (2H, t, J=8 Hz), 2.00 (2H, m).

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-0439513f40f94e1c886cf07268c72c20
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…