HCID 13959887, compound → HCID 14050839, compound

HRID 2232083Notes

Reaction equation

HRID 2232083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].[C:22]([NH:25][CH2:26][CH:27]1[CH:31]([Cl:32])[CH2:30][NH:29][CH2:28]1)(=[O:24])[CH3:23]>CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:29]1[CH2:30][CH:31]([Cl:32])[CH:27]([CH2:26][NH:25][C:22](=[O:24])[CH3:23])[CH2:28]1)[N:8]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21]

Participants

4

Reactant 2

HCID 13959887HCID 13959887, compoundHCID 14347793HCID 14347793, compound

Product 1

HCID 14050839HCID 14050839, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

6,7-Difluoro-1-(2-thienyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.5 g) and 3-acetylaminomethyl-4-chloropyrrolidine (0.86 g) are added to N-methylpyrrolidone (50 ml) and the mixture is stirred at 110° C. for one hour. After the reaction, the solvent is distilled off and the resulting residue is crystallized with ethanol. The crystals are separated by filtration and then recrystallized from ethanol to give 6-fluoro-1-(2-thienyl)7-(3-acetylaminomethyl-4-chloro-1-pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.54 g) powder, m.p. 145° C. (decomp.).

Workup

  1. customAfter the reaction
  2. distillationthe solvent is distilled off
  3. customthe resulting residue is crystallized with ethanol
  4. customThe crystals are separated by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0b954bc8545b458fb37b53d48bcdf4a8
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

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