2-Methoxyethylamine → 1-(cyanomethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364504Notes

Reaction equation

HRID 2364504 reaction equation
[C:1]([CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23](OCC)=[O:24])[C:5]1=[O:28])#[N:2].[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>>[C:1]([CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:33][CH2:32][CH2:31][O:30][CH3:29])=[O:24])[C:5]1=[O:28])#[N:2]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 86612794HCID 86612794, compound

Product 1

HCID 866127951-(cyanomethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 40%

Procedure

In a similar manner to that described in example 196, from ethyl 1-(cyanomethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (33 mg, 0.087 mmol) and [2-(methyloxy)ethyl]amine (0.05 mL) was prepared 1-(cyanomethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (14 mg, 40% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 9.95 (s, 1 H), 8.62 (s, 1 H), 7.38 (s, 1 H), 7.18-7.15 (m, 2 H), 7.05-7.01 (m, 2 H), 5.12 (s, 2 H), 4.17 (s, 2 H), 3.63 (m, 2 H), 3.57 (m, 2 H), 3.41 (s, 3 H); MS m/z 411 (M+1).

Sources & evidence

ORD record
ord-f573f94bb0e5406da1d85c35da9cc324
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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