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

HRID 2364412Notes

Reaction equation

HRID 2364412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([O:22]CC)=O)[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:26][CH2:27][CH2:28][N:29]([CH3:34])[S:30]([CH3:33])(=[O:32])=[O:31]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([NH:26][CH2:27][CH2:28][N:29]([CH3:34])[S:30]([CH3:33])(=[O:32])=[O:31])=[O:22])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 28707509N-(2-aminoethyl)-N-methylmethanesulfonamideHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694828877-[(4-Fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and N-(2-aminoethyl)-N-methylmethanesulfonamide employing methods similar to those described in Example 2 and using N,N-dimethylformamide as the reaction solvent. The product was obtained as an off-white solid: 1H NMR (d6-DMSO) δ 11.93 (1H, br s), 10.91 (1H, br s), 9.99 (1H, br s), 8.10 (1H, br s), 7.35-7.25 (3H, m), 7.18-7.08 (2H, m), 3.98 (2H, br s), 3.46 (2H, br s), 3.21 (2H, br s), 2.85 (3H, s), 2.81 (3H, s); HRMS calcd for C20H21FN4O5S+H+: 449.1295. Found 449.1292.

Workup

  1. customThe product was obtained as an off-white solid

Sources & evidence

ORD record
ord-c6a2ef7fc91a4f3dbadf6e6f7aa0d971
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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