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

HRID 2364293Notes

Reaction equation

HRID 2364293 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:26])=[C:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][NH:32][C:31]1=[O:35]>>[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:26])=[C:14]([C:21]([NH:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][NH:32][C:31]4=[O:35])=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80480N-(2-Aminoethyl)ethyleneureaHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694804397-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 98%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (10 mg, 0.028 mmol) described in example 92 and 1-(2-aminoethyl)-2-imidazolidinone (47 mg, 0.364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (12 mg, 98% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.33 (br s, 1 H), 8.54 (s, 1 H), 7.37 (s, 1 H), 7.16-7.13 (m, 2 H), 7.03-6.99 (m, 2 H), 4.38 (s, 1 H), 4.12 (s, 2 H), 3.62 (m, 2 H), 3.56-3.53 (m, 5 H), 3.45-3.39 (m, 4 H); HRMS m/z calcd for C22H23N5O4F: 440.1734 Found: 440.1732.

Sources & evidence

ORD record
ord-edb5b76dcd8845e1a7ea61090603bd2a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…