Ethanolamine → HCID 69958994, compound

HRID 369275Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26].[CH2:27]([CH2:29][NH2:30])[OH:28]>N1C=CC=CC=1>[CH2:27]([CH2:29][NH2:30])[OH:28].[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:30][CH2:29][CH2:27][OH:28])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26]

Participants

Conditions

Temperature: 50 °C

Procedure

1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (300 mg) and ethanolamine (300 mg) were added to pyridine (1,300 mg), and the mixture was stirred at 50° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Ethanol (4 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (290 mg) as a colorless powder.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
concentrationA process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure
additionEthanol (4 ml) was added to the resultant residue, and deposits
filtrationwere collected by filtration
washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record: ord-e543cc30c5d34584b902c87db51f8b28
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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