Fluoroquinolonic acid → HCID 13772815, compound

HRID 868091Notes

Reaction equation

HRID 868091 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH2:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[CH3:21]>N1C=CC=C(C)C=1>[ClH:1].[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:26]4[CH2:27][CH2:28][CH:24]([CH2:23][NH:22][CH2:20][CH3:21])[CH2:25]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 483180Fluoroquinolonic acidHCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 13772815HCID 13772815, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 79703-MethylpyridineSolvent

Procedure

A solution of 0.57 g (2.0 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.58 ml (4.0 mmol) of 3-[(ethylamino)methyl]pyrrolidine and 10 ml of 3-picoline was heated under reflux for 17 hours. After cooling to room temperature the mixture was filtered and the solid washed with hot methanol to give 0.42 g of the title compound, mp >300° C.

Workup

  1. temperatureunder reflux for 17 hours
  2. filtrationwas filtered
  3. washthe solid washed with hot methanol

Sources & evidence

ORD record
ord-5119977f21e54e22834eeb6e24bec126
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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