N-(2-Aminoethyl)ethyleneurea → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364388Notes

Reaction equation

HRID 2364388 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:29])=[C:14]([C:24](OCC)=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:30][CH2:31][CH2:32][N:33]1[CH2:37][CH2:36][NH:35][C:34]1=[O:38]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:29])=[C:14]([C:24]([NH:30][CH2:31][CH2:32][N:33]4[CH2:37][CH2:36][NH:35][C:34]4=[O:38])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 80480N-(2-Aminoethyl)ethyleneureaHCID 69481032HCID 69481032, compound

Product 1

HCID 694804577-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 31%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (60 mg, 0.15 mmol) and 1-(2-aminoethyl)-2-imidazolidinone (0.4 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (22 mg, 31% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.25 (br s, 1 H), 8.55 (s, 1 H), 7.46 (s, 1 H), 7.16-7.12 (m, 2 H), 7.03-7.12 (m, 2 H), 4.73 (br s, 1 H), 4.29 (br s, 2 H), 4.11 (s, 2 H), 3.64-3.39 (m, 10 H), 1.79 (m, 2 H); HRMS m/z calcd for C24H27N5O5F: 484.1996. Found: 484.1997.

Sources & evidence

ORD record
ord-b49ab8a59ba74e3d895338b26ee7c16d
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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