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

HRID 2364498Notes

Reaction equation

HRID 2364498 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:34])=[C:14]([C:29](OCC)=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:35][CH:36]([O:38][CH2:39][CH2:40][CH2:41][NH2:42])[CH3:37]>>[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:34])=[C:14]([C:29]([NH:42][CH2:41][CH2:40][CH2:39][O:38][CH:36]([CH3:37])[CH3:35])=[O:30])[C:15](=[O:28])[N:16]3[CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3=[O:27])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 761943-IsopropoxypropylamineHCID 69482570Ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694809757-[(4-Fluorophenyl)methyl]-4-hydroxy-N-{3-[(1-methylethyl)oxy]propyl}-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 3-[(1-methylethyl)oxy]-1-propanamine using methods similar to Example 563 to provide a white solid: ES+ MS: 539 (M+H+).

Workup

  1. customto provide a white solid

Sources & evidence

ORD record
ord-728ac75b457c4588af6a0f608f10ed73
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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