Ethanolamine → 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364320Notes

Reaction equation

HRID 2364320 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].[NH2:30][CH2:31][CH2:32][OH:33]>>[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:30][CH2:31][CH2:32][OH:33])=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482001HCID 69482001, compound

Product 1

HCID 694808821-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 43%

Procedure

In a similar manner to that described in example 196, from ethyl 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.050 mmol) and 2-aminoethanol (0.05 mL), was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (9 mg, 43% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.48 (br s, 1 H), 8.55 (s, 1 H), 7.27 (s, 1 H), 7.18-7.15 (m, 2 H), 7.05-7.01 (m, 2 H), 4.14 (s, 2 H), 4.07 (m, 2 H), 3.85 (m, 2 H), 3.63 (m, 2 H), 1.51 (m, 2 H), 1.33 (m, 2 H), 0.90 (m, 3 H); MS m/z 414 (M+1).

Sources & evidence

ORD record
ord-cd03b6cf29564387a09a666b4ce2b7fc
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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