Ethoxyethylamine → N-[2-(Ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364497Notes

Reaction equation

HRID 2364497 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:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:35]([O:37][CH2:38][CH2:39][NH2:40])[CH3:36]>>[CH2:35]([O:37][CH2:38][CH2:39][NH:40][C:29]([C:14]1[C:15](=[O:28])[N:16]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]2=[O:27])[C:17]2[C:12]([C:13]=1[OH:34])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:18]=2)=[O:30])[CH3:36]

Participants

3

Reactant 2

HCID 66970EthoxyethylamineHCID 69482570Ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69480880N-[2-(Ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)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-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-(ethyloxy)ethanamine using methods similar to Example 563 to provide a white solid: 1H NMR (CDCl3) δ 10.36 (1H, b), 8.53 (1H, s), 8.16 (1H, s), 7.37 (2H, dd, J=6, 8 Hz), 7.11 (2H, t, J=9 Hz), 4.37 (2H, t, J=6 Hz), 4.13 (2H, s), 3.42-3.50 (8H, m), 3.24 (2H, t, J=6 Hz), 1.99 (2H, t, J=6 Hz), 1.48-1.62 (4H, m), 1.10 (3H, t, J=7 Hz); ES+ MS: 511 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-64a617c531d24d6cab48b9cf99e91300
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…