Diethylamine → 6-[(3-chloro-4-fluoro-phenyl)methyl]-N,N-diethyl-4-hydroxy-2-methyl-3,5-dioxo-7,8-dihydro-2,6-naphthyridine-1-carboxamide

HRID 1817341Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:22]C)[C:10](=[O:21])[N:11]([CH3:20])[C:12]=2[C:16]([O:18]C)=O)[C:7]1=[O:24].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:22])[C:10](=[O:21])[N:11]([CH3:20])[C:12]=2[C:16]([N:31]([CH2:32][CH3:33])[CH2:29][CH3:30])=[O:18])[C:7]1=[O:24]

Participants

Reactant 2

HCID 8021Diethylamine

HCID 69058384Methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 546818736-[(3-chloro-4-fluoro-phenyl)methyl]-N,N-diethyl-4-hydroxy-2-methyl-3,5-dioxo-7,8-dihydro-2,6-naphthyridine-1-carboxamide

Procedure

The title compound was prepared from methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate in a manner similar to that described in Example 12, Steps 12, 13 and 14, using diethyl amine in place of dimethylamine in the step corresponding to Step 13 of Example 12.

Sources & evidence

ORD record: ord-7c90e7c47941423ba112e40a61765455
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598264B2

Reaction notes

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