Triethylamine → HCID 23284744, compound

HRID 369306Notes

Reaction equation

HRID 369306 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].[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].C(N(CC)CC)C>N1C=CC=CC=1>[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:27][CH2:28][CH2:29][CH2:30][OH:31])[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

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 23284744HCID 23284744, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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), 3-amino-1-propanol (75 mg) and triethylamine (110 mg) were added to pyridine (400 mg), and the mixture was stirred at 40° C. for 65 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 (100 mg) was added to the residue, and the mixture was concentrated under reduced pressure. 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 (85 mg) as a pale yellow 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 (100 mg) was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionEthanol (1.5 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-14656a69bae748ba92443c0ff1ad800c
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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