Methylamine → HCID 23284781, compound

HRID 369278Notes

Reaction equation

HRID 369278 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:28])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([NH:20][CH2:21][CH2:22][OH:23])[N:13]=1)[CH:9]=[C:8]([C:24]([OH:26])=[O:25])[C:7]2=[O:27].[CH3:30][NH2:31]>C(O)(C)C>[Cl:1][C:2]1[C:3]([NH:31][CH3:30])=[C:4]([F:28])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([NH:20][CH2:21][CH2:22][OH:23])[N:13]=1)[CH:9]=[C:8]([C:24]([OH:26])=[O:25])[C:7]2=[O:27]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23284746HCID 23284746, compound

Product 1

HCID 23284781HCID 23284781, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8-Chloro-6,7-difluoro-1-[3,5-difluoro-6-(2-hydroxyethylamino)pyridin-2-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (250 mg) and an aqueous solution (about 40%; 3 g) of methylamine were added to isopropyl alcohol (4 ml), and the mixture was stirred at room temperature for 15 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. Ethanol (2 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 (175 mg) as a pale brown 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. additionEthanol (2 ml) was added to the resultant residue, and deposits
  4. filtrationwere collected by filtration
  5. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-b887420aae6c443397f79d9beef600c5
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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