N-(2-aminoethyl)acetamide → N-[2-(acetylamino)ethyl]-1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364446Notes

Reaction equation

HRID 2364446 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][NH:33][C:34](=[O:36])[CH3:35]>>[C:34]([NH:33][CH2:32][CH2:31][NH:30][C:24]([C:7]1[C:6](=[O:29])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]2[C:9]([C:8]=1[OH:23])=[N:10][CH:11]=[C:12]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH:13]=2)=[O:25])(=[O:36])[CH3:35]

Participants

3

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 69482001HCID 69482001, compound

Product 1

HCID 69482078N-[2-(acetylamino)ethyl]-1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 59%

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 (30 mg, 0.075 mmol) and N-(2-aminoethyl)acetamide (27 mg, 0.264 mmol) was prepared N-[2-(acetylamino)ethyl]-1-butyl-7-[(4fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 59% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.41 (br s, 1 H), 8.55 (s, 1 H), 7.27 (s, 1 H), 8.17-7.13 (m, 2 H), 7.05-7.01 (m, 2 H), 6.18 (br s, 1 H), 4.13 (s, 2 H), 4.06 (m, 2 H), 3.59 (m, 2 H), 3.47 (m, 2 H), 1.97 (s, 3 H), 1.52 (m, 2 H), 1.33 (m, 2 H), 0.90 (m, 3 H); MS m/z 455 (M+1).

Sources & evidence

ORD record
ord-17321384d1564241913cd28ec2b26b6c
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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