N-(2-aminoethyl)-N-methylmethanesulfonamide → 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364447Notes

Reaction equation

HRID 2364447 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][N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35]>>[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:30][CH2:31][CH2:32][N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 28707509N-(2-aminoethyl)-N-methylmethanesulfonamideHCID 69482001HCID 69482001, compound

Product 1

HCID 694809821-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 55%

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)-N-methylmethanesulfonamide (excess) was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (21 mg, 55% 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), 7.17-7.13 (m, 2 H), 7.05-7.00 (m, 2 H), 4.13 (s, 2 H), 4.08 (m, 2 H), 3.65 (m, 2 H), 3.39 (m, 2 H), 2.94 (s, 3 H), 2.82(s, 3 H), 1.50 (m, 2 H), 1.33 (m, 2 H), 0.89 (m, 3 H); MS m/z 505 (M+1).

Sources & evidence

ORD record
ord-cf6bbc96555243eba80890f6b3135e57
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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