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

HRID 2364358Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22](OCC)=[O:23])[C:4]1=[O:27])[CH3:2].[NH2:28][CH2:29][CH2:30][OH:31]>>[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([NH:28][CH2:29][CH2:30][OH:31])=[O:23])[C:4]1=[O:27])[CH3:2]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 69482004HCID 69482004, compound

Product 1

HCID 694825661-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 58%

Procedure

In a similar manner to that described in example 196, from ethyl 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.081 mmol) and 2-aminoethanol (0.05 mL) was prepared 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (18 mg, 58% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.47 (br s, 1 H), 8.53 (s, 1 H), 7.35 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.99 (m, 2 H), 4.20-4.13 (m, 4 H), 3.85 (m, 2 H), 3.63 (m, 2 H), 1.22 (m, 3 H); HRMS m/z calcd for C20H21FN3O4: 386.1510. Found: 386.1517.

Sources & evidence

ORD record: ord-e65f3887fd6944dfb0f018d59cba8f66
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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