1-Amino-2-propanol → 7-[(4-Fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364495Notes

Reaction equation

HRID 2364495 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.[NH2:35][CH2:36][CH:37]([OH:39])[CH3:38]>>[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]([NH:35][CH2:36][CH:37]([OH:39])[CH3:38])=[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

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 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 694827897-[(4-Fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-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 1-amino-2-propanol using methods similar to Example 563 to provide a white solid: 1H NMR (CDCl3) δ 10.42 (1H, b), 8.56 (1H, s), 8.30 (1H, s), 7.25 (2H, dd, J=5, 9 Hz), 6.99 (2H, dd, J=9 Hz), 4.39 (2H, t, J=7 Hz), 4.16 (2H, s), 4.04-4.12 (1H, m), 3.60-3.67 (1H, m), 3.54 (2H, t, J=8 Hz), 3.34-3.42 (3H, m), 2.36 (2H, b), 1.73-1.80 (4H, m), 1.28 (3H, d, J=6 Hz); ES+ MS: 497 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-9c50b08ab20d4304bed7004d2f1e255e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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