3-Amino-1-propanol → HCID 69480877, compound

HRID 2364449Notes

Reaction equation

HRID 2364449 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[NH2:32][CH2:33][CH2:34][CH2:35][OH:36].[OH-].[Na+:38]>>[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([O-:23])=[C:7]([C:24]([NH:32][CH2:33][CH2:34][CH2:35][OH:36])=[O:25])[C:6]1=[O:29].[Na+:38]

Participants

4

Reactant 3

HCID 90863-Amino-1-propanolHCID 14798Sodium HydroxideHCID 58882926HCID 58882926, compound

Product 1

HCID 69480877HCID 69480877, compound

Procedure

This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 3-amino-1-propanol employing methods similar to those described in Example 245. The resulting material was triturated with water, covered with EtOH and treated with 1 equivalent of 1N NaOH solution. Concentration in vacuo afforded the product as a white solid: 1H NMR (d6-DMSO) δ 10.53 (1H, br), 8.14 (1H, s), 7.25 (3H, m), 7.10 (2H, t, J=9 Hz), 4.92 (2H, s), 4.49 (1H, br), 3.98 (2H, s), 3.43 (2H, m), 3.25 (2H, m), 3.07 (3H, s), 2.78 (3H, s), 1.58 (2H, m, J=6 Hz); AP+ MS: 457 (M+H+, 100).

Workup

  1. customThe resulting material was triturated with water
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-1bd79213ffcb494c838adc1bdff36f62
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…