1H-Imidazole-1-propanamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(1H-imidazol-1-yl)propyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364301Notes

Reaction equation

HRID 2364301 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.[N:27]1([CH2:32][CH2:33][CH2:34][NH2:35])[CH:31]=[CH:30][N:29]=[CH:28]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:35][CH2:34][CH2:33][CH2:32][N:27]4[CH:31]=[CH:30][N:29]=[CH:28]4)=[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 787361H-Imidazole-1-propanamineHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694822717-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(1H-imidazol-1-yl)propyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 33%

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 [3-(1H-imidazol-1-yl)propyl]amine (48 mg, 0.0384 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(1H-imidazol-1-yl)propyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (4 mg, 33% yield), as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.36 (br s, 1 H), 8.59 (s, 1 H), 7.74 (s, 1 H), 7.42 (s, 1 H), 7.18-7.14 (m, 2 H), 7.12 (s, 1 H), 7.05-7.01 (m, 3 H), 4.15 (s, 2 H), 4.11-4.07 (m, 2 H), 3.59 (s, 3 H), 3.51-3.45 (m, 2 H), 2.19-2.12 (m, 2 H); MS m/z 436 (M+1).

Sources & evidence

ORD record
ord-5a68511e35a44764a88722aa8aa2b1b4
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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