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

HRID 2364319Notes

Reaction equation

HRID 2364319 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][CH:32]([OH:34])[CH3:33]>>[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][CH:32]([OH:34])[CH3:33])=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 69482001HCID 69482001, compound

Product 1

HCID 694801871-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 38%

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 1-amino-2-propanol (0.05 mL), was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (8 mg, 38% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.50 (br s, 1 H), 8.57 (s, 1 H), 7.28 (s, 1 H), 7.19-7.15 (m, 2 H), 7.07-7.02 (m, 2 H), 4.14 (s, 2 H), 4.11-4.07 (m, 3 H), 3.61 (m, 1 H), 3.39 (m, 1 H), 1.57-1.49 (m, 2 H), 1.38-1.24 (m, 6 H), 0.91 (m, 3 H); MS m/z 428 (M+1).

Sources & evidence

ORD record
ord-c943548826254038a4d7ac12ef67f306
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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