Valinol → HCID 69482170, compound

HRID 2364480Notes

Reaction equation

HRID 2364480 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.[NH2:34][CH:35]([CH:38]([CH3:40])[CH3:39])[CH2:36][OH: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:34][CH:35]([CH2:36][OH:37])[CH:38]([CH3:40])[CH3:39])=[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 79019ValinolHCID 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 69482170HCID 69482170, compound

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-amino-3-methyl-1-butanol using conditions similar to those employed in Example 563 to provide a white solid: 1H NMR (d6-DMSO) δ 10.38 (1H, d, J=9 Hz), 8.55 (1H, s), 8.14 (1H, s), 7.40 (2H, dd, J=6, 9 Hz), 7.13 (2H, t, J=9 Hz), 4.87 (1H, t, J=5 Hz), 4.30-4.50 (2H, m), 4.16 (2H, s), 3.79-3.87 (1H, m), 3.32-3.60 (7H, m), 1.89-2.04 (2H, m), 1.71-1.81 (2H, m), 0.90 (6H, dd, J=7, 9 Hz); ES+ MS: 511 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-fbac871ccacb4742ba7232ae5f93623c
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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