5-(Aminomethyl)pyridin-2(1H)-one → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[(6-oxo-1,6-dihydro-3-pyridinyl)methyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364296Notes

Reaction equation

HRID 2364296 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](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32](=[O:35])[NH:33][CH:34]=1>>[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][C:29]4[CH:30]=[CH:31][C:32](=[O:35])[NH:33][CH:34]=4)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 148469815-(Aminomethyl)pyridin-2(1H)-oneHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694820457-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[(6-oxo-1,6-dihydro-3-pyridinyl)methyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 58%

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(10 mg, 0.028 mmol) described in example 92 and 5-(aminomethyl)-2(1H)-pyridinone (50 mg, 0.403 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[(6-oxo-1,6-dihydro-3-pyridinyl)methyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (7 mg, 58% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.51 (br s, 1 H), 8.59 (s, 1 H), 7.49 (d, J=9.6 Hz, 1 H), 7.39 (s, 2 H), 7.17-7.13 (m, 2 H), 7.04-6.94 (m, 2 H), 6.56 (d, J=9.6 Hz, 1 H), 4.38 (d, J=6 Hz, 2 H), 4.13 (s, 2 H), 3.56 (s, 3 H); HRMS m/z calcd for C23H20N4O4F: 435.1469 Found: 435.1470.

Sources & evidence

ORD record
ord-70750967cd674cbda0977b83e479a3a5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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