Ethyl 3-chloro-3-oxopropionate → Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 2364141Notes

Reaction equation

HRID 2364141 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])[C:10]([C:13](OCC)=[O:14])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.Cl[C:30](=[O:37])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:8]=[C:9]3[C:10]([C:13]([OH:14])=[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:30](=[O:37])[N:18]3[CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])=[N:11][CH:12]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 58882948Ethyl 5-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethyl]amino}pyridine-2-carboxylate

Product 1

HCID 58882907Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Procedure

This compound was prepared from ethyl 5-(4-fluorobenzyl)-3-{[2-(2-oxopyrrolidin-1-yl)ethyl]amino}pyridine-2-carboxylate and ethyl 3-chloro-3-oxopropionate in a manner similar to that described in Example 1, Steps 10-11 and was obtained as a white solid: 1H NMR (CDCl3) δ 8.50 (1H, d, J=1.4 Hz), 8.11 (1H, s), 7.26 (2H, m), 7.00 (2H, ddd, J˜9, 9, 2 Hz), 4.52 (2H, q, J=7 Hz), 4.33 (2H, br t, J˜7 Hz), 4.14 (2H, s), 3.52-3.44 (4H, m), 2.35 (2H, t, J=8 Hz), 2.00 (2H, m), 1.48 (3H, t, J=7 Hz); HRMS calcd for C24H24FN3O5+H+: 454.1778. Found: 454.1787.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-7a837cd1213e4b468f6bb245c3b51366
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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