2-Amino-1-pentanol → HCID 69482604, compound

HRID 2364481Notes

Reaction equation

HRID 2364481 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]([CH2:38][CH2:39][CH3:40])[CH2:36][OH:37]>>[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]([NH:34][CH:35]([CH2:36][OH:37])[CH2:38][CH2:39][CH3:40])=[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

Participants

3

Reactant 2

HCID 2490172-Amino-1-pentanolHCID 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 69482604HCID 69482604, 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-1-pentanol using conditions similar to those employed in Example 563 to provide a white solid: 1H NMR (d6-DMSO) δ 10.31 (1H, d, J=8 Hz), 8.55 (1H, s), 8.12 (1H, s), 7.40 (2H, dd, J=6, 9 Hz), 7.13 (2H, t, J=9 Hz), 4.93 (1H, t, J=5 Hz), 4.30-4.46 (2H, m), 4.15 (2H, s), 3.94-4.03 (1H, m), 3.32-3.53 (6H, m), 1.88-2.05 (2H, m), 1.68-1.82 (2H, m), 1.42-1.64 (2H, m), 1.25-1.36 (2H, m), 0.88 (3H, t, J=7 Hz); ES+ MS: 511 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-25473f8f99754499bfcea48f96db0718
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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