(2R)-1-aminopropan-2-ol → HCID 54417394, compound

HRID 369321Notes

Reaction equation

HRID 369321 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][C@H: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][C@H: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]=1

Participants

4

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 54417394HCID 54417394, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg) and (R)-1-amino-2-propanol (150 mg) were added to pyridine (450 mg), and the mixture was stirred at 55° 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. Concentrated hydrochloric acid (150 mg) was added to the resultant 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 (164 mg) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionConcentrated hydrochloric acid (150 mg) was added to the resultant residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionEthanol (1 ml) was added to the resultant residue, and deposits
  6. filtrationwere collected by filtration
  7. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-04547e874eb041e7bddfb9e2caee9fa5
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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