Allylamine → HCID 23284810, compound

HRID 369307Notes

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

Participants

Conditions

Temperature: 40 °C

Procedure

1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg), allylamine (35 mg) and triethylamine (300 mg) were added to pyridine (400 mg), and the mixture was stirred for 2 hours at 40° C. and for 63 hours at room temperature. 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 (1.5 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 (100 mg) as a pale brown 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 (1.5 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-23f27229e63f4f738f12fa88321be1e1
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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