Ethanolamine → HCID 484063, compound

HRID 369314Notes

Reaction equation

HRID 369314 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[CH3:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.[CH2:27]([CH2:29][NH2:30])[OH:28].CN1CCCC1>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:30][CH2:29][CH2:27][OH:28])[C:16]=3[CH3:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 84541-MethylpyrrolidineHCID 11132289HCID 11132289, compound

Product 1

HCID 484063HCID 484063, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (500 mg), monoethanolamine (410 mg) and N-methylpyrrolidine (170 mg) were added to pyridine (1,500 mg), and the mixture was stirred at 90° C. for 71 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (1.5 ml) to the residue and then concentrating the mixture under reduced pressure was conducted 3 times repeatedly. The resultant residue was subjected to column chromatography (silica gel: 15 g, eluent; chloroform:methanol=50:1→10:1). Ethanol (0.5 ml) was added to a concentrate of a fraction containing a main product, and the mixture was stirred at room temperature. Deposits formed were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (62 mg) as a brown powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (1.5 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionEthanol (0.5 ml) was added to
  4. concentrationa concentrate of a fraction
  5. additioncontaining a main product
  6. stirringthe mixture was stirred at room temperature
  7. customDeposits formed
  8. filtrationwere collected by filtration
  9. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-64b1f9a204094bd6bca13eead375a307
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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