Triethylamine → HCID 131714524, compound

HRID 1589571Notes

Reaction equation

HRID 1589571 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:9]1[N:18]=[C:17]2[C:12]([C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15][N:16]2[CH:19]2[CH2:21][CH2:20]2)=[CH:11][C:10]=1[F:26].[Br:27][CH2:28][CH2:29][OH:30].C(N(CC)CC)C>CN(C=O)C>[BrH:27].[CH:19]1([N:16]2[C:17]3[C:12](=[CH:11][C:10]([F:26])=[C:9]([N:2]4[CH2:3][CH:4]5[CH2:7][CH2:8][CH:1]4[CH2:6][N:5]5[CH2:28][CH2:29][OH:30])[N:18]=3)[C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15]2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 13565798HCID 13565798, compound

Product 1

HCID 131714524HCID 131714524, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.77 g (2.0 mmol) of 7-(2,5-diazabicyclo[2.2.2]oct-2-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 0.70 ml (8.0 mmol) of 2-bromoethanol, 1.30 ml (8.0 mmol) of triethylamine, and 20 ml of DMF was heated at 100° C. for 18 hours. The reaction solution was evaporated to dryness and the residue was triturated ethanol. The solid was collected by filtration to give 0.61 g of the title product, mp 290° C. dec (a).

Workup

  1. customThe reaction solution was evaporated to dryness
  2. customthe residue was triturated ethanol
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-1be6f36511194594b37568aba07cf8a5
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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