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

HRID 2364313Notes

Reaction equation

HRID 2364313 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:26])=[C:14]([C:21]([O:23]CC)=O)[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][CH2:28][CH2:29][N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32]>>[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:26])=[C:14]([C:21]([NH:27][CH2:28][CH2:29][N:30]([CH3:35])[S:31]([CH3:34])(=[O:33])=[O:32])=[O:23])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 28707509N-(2-aminoethyl)-N-methylmethanesulfonamideHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694809727-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 96%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.056 mmol) described in example 92 and N-(2-aminoethyl)-N-methylmethanesulfonamide (55 mg, 0.364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (24 mg, 96% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.39 (br s, 1 H), 8.55 (s, 1 H), 7.38 (s, 1 H), 7.16-7.12 (m, 2 H), 7.03-6.99 (m, 2 H), 4.12 (s, 2 H), 3.68-3.63 (m, 2 H), 3.56 (s, 3 H), 3.42-3.38 (m, 2 H), 2.94 (s, 3 H), 2.82 (s, 3 H). HRMS m/z calcd for C21H24N4O5FS: 463.1451; Found: 463.1443.

Sources & evidence

ORD record
ord-2272a3e051a9414a9636d99374ad6312
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…