1-Amino-2-propanol → HCID 23284697, compound
Reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[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)[CH:7]=1.[NH2:27][CH2:28][CH:29]([OH:31])[CH3:30]>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH2:28][CH:29]([OH:31])[CH3:30])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1Participants
Conditions
- Temperature
- 45 °C
Procedure
1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg) and 1-amino-2-propanol (150 mg) were added to pyridine (500 mg), and the mixture was stirred at 45° C. for 16 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. Concentrated hydrochloric acid (150 mg) was added to the residue, and the mixture was concentrated under reduced pressure. Ethanol (1 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 (157 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
- additionConcentrated hydrochloric acid (150 mg) was added to the residue
- concentrationthe mixture was concentrated under reduced pressure
- additionEthanol (1 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-8e64b4f5230344fdadbb64bc2d359b78
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136823
Reaction notes
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