3-Isopropoxypropylamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{3-[(1-methylethyl)oxy]propyl}-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364472Notes

Reaction equation

HRID 2364472 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26](OCC)=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:34][CH:35]([O:37][CH2:38][CH2:39][CH2:40][NH2:41])[CH3:36]>>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:26]([NH:41][CH2:40][CH2:39][CH2:38][O:37][CH:35]([CH3:36])[CH3:34])=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 761943-IsopropoxypropylamineHCID 58882907Ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-oxopyrrolidin-1-yl ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694826757-[(4-fluorophenyl)methyl]-4-hydroxy-N-{3-[(1-methylethyl)oxy]propyl}-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 3-[(1-methylethyl)oxy]-1-propanamine using conditions similar to those employed in Example 563 to provide a white solid: ES+ MS: 525 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-4d8b4a2ea45348859338558923517bc2
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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