1-(3-Aminopropyl)-2-pyrrolidinone → HCID 69482728, compound

HRID 2364476Notes

Reaction equation

HRID 2364476 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][CH2:35][CH2:36][CH2:37][N:38]1[CH2:42][CH2:41][CH2:40][C:39]1=[O:43]>>[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][CH2:35][CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][C:39]4=[O:43])=[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 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 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 69482728HCID 69482728, 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 1-(3-aminopropyl)-2-pyrrolidinone using conditions similar to those employed in Example 563 to provide a white solid: 1H NMR (d6-DMSO) δ 10.28 (1H, t, J=6 Hz), 8.55 (1H, s), 8.10 (1H, s), 7.40 (2H, dd, J=6, 9 Hz), 7.13 (2H, t, J=9 Hz), 4.37 (2H, t, J=6 Hz), 4.15 (2H, s), 3.43 (2H, t, J=6 Hz), 3.31-3.39 (6H, m), 3.22 (2H, t, J=7 Hz), 2.22 (2H, t, J=8 Hz), 1.87-2.00 (4H, m), 1.70-1.78 (4H, m); ES+ MS: 550 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-4691d8af2d464909b16366eab96021d1
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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