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

HRID 2364353Notes

Reaction equation

HRID 2364353 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([O:24]CC)=O)[C:4]1=[O:27])[CH3:2].[NH2:28][CH2:29][CH2:30][N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33]>>[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([NH:28][CH2:29][CH2:30][N:31]([CH3:36])[S:32]([CH3:35])(=[O:34])=[O:33])=[O:24])[C:4]1=[O:27])[CH3:2]

Participants

3

Reactant 2

HCID 28707509N-(2-aminoethyl)-N-methylmethanesulfonamideHCID 69482004HCID 69482004, compound

Product 1

HCID 694802731-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 67.2%

Procedure

In a similar manner to that described in example 196, from ethyl 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (38 mg, 0.103 mmol), and N-(2-aminoethyl)-N-methylmethanesulfonamide (489 mg, 3.21 mmol), was prepared 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (33 mg, 67% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.42 (br s, 1 H), 8.55 (s, 1 H), 7.38 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.99 (m, 2 H), 4.19 (m, 2 H), 4.14 (s, 2 H), 3.66 (m, 2 H), 3.41 (m, 2 H), 2.97 (s, 3 H), 2.84 (s, 3 H), 1.23 (m, 3 H); HRMS m/z calcd for C22H26FN4O5S: 477.1602. Found: 477.1610.

Sources & evidence

ORD record
ord-e6595a965a6c478e8d5aafdfc8dc0169
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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