Methylamine → 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364282Notes

Reaction equation

HRID 2364282 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27]([O:29]CC)=O)[C:9]2=[O:32])=[CH:4][CH:3]=1.[CH3:33][NH2:34]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27]([NH:34][CH3:33])=[O:29])[C:9]2=[O:32])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694822621-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to that described in example 196, from ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (22 mg, 0.0504 mmol) and methylamine (0.1 mL of a 8 M solution in ethanol) was prepared 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (6 mg, 29% yield) as a tan solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 9.87 (br s, 1 H), 8.52 (s, 1 H), 7.30-7.24 (m, 2 H), 7.20-7.16 (m, 2 H), 7.01-6.91 (m, 4 H), 6.71 (s, 1 H), 3.94 (s, 2 H), 2.96 (d, J=4.8 Hz, 3 H); MS m/z 422 (M+1).

Sources & evidence

ORD record
ord-740e4567f9b046d5b5498a17e428bc94
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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