2-Morpholinoethylamine → 7(4-Fluorobenzyl)-4-hydroxy-N-(2-morpholin-4-ylethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364143Notes

Reaction equation

HRID 2364143 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.[CH2:34]1[N:39]([CH2:40][CH2:41][NH2:42])[CH2:38][CH2:37][O:36][CH2:35]1>>[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:42][CH2:41][CH2:40][N:39]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[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 4082852-MorpholinoethylamineHCID 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 547221247(4-Fluorobenzyl)-4-hydroxy-N-(2-morpholin-4-ylethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

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-(4-morpholino)ethylamine employing methods similar to those described in Example 5. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). This procedure gave the product as an off-white rigid foam: 1H NMR (CDCl3) δ 10.46 (1H, br t, J˜6 Hz), 8.59 (1H, d, J=1.3 Hz), 8.12 (1H, s), 7.24 (2H, dd, J=8.6, 5.4 Hz), 7.00 (2H, t, J=8.6 Hz), 4.32 (2H, br t, J=7 Hz), 4.16 (2H, s), 3.98 (4H, br), 3.91 (2H, q, J=6 Hz), 3.77 (2H, br), 3.50 (4H, m), 3.39 (2H, t, J=6 Hz), 2.92 (2H, br), 2.41 (2H, t, J=8 Hz), 2.05 (2H, m); ES+ MS: 538 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)

Sources & evidence

ORD record
ord-663e0ffd739c46cdb513f1ca7ec9e7b6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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