Ethyl propiolate → 8-Cyano-1-cyclopropyl-7-[(1S,6S)-2-(2-ethloxycarbonyl-vinyl)2,8-diazabicyclo[4.3.0]nonan-8-yl-]6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 651279Notes

Reaction equation

HRID 651279 reaction equation
[C:1]([C:3]1[C:4]([N:21]2[CH2:29][C@@H:28]3[C@@H:23]([CH2:24][CH2:25][CH2:26][NH:27]3)[CH2:22]2)=[C:5]([F:20])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8]2=[O:19])#[N:2].[C:30]([O:34][CH2:35][CH3:36])(=[O:33])[C:31]#[CH:32]>>[C:1]([C:3]1[C:4]([N:21]2[CH2:29][C@@H:28]3[C@@H:23]([CH2:24][CH2:25][CH2:26][N:27]3[CH:32]=[CH:31][C:30]([O:34][CH2:35][CH3:36])=[O:33])[CH2:22]2)=[C:5]([F:20])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:14][CH2:15]1)[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8]2=[O:19])#[N:2]

Participants

3

Reactant 2

HCID 12182Ethyl propiolateHCID 9802884Pradofloxacin

Product 1

HCID 702454038-Cyano-1-cyclopropyl-7-[(1S,6S)-2-(2-ethloxycarbonyl-vinyl)2,8-diazabicyclo[4.3.0]nonan-8-yl-]6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Procedure

400 mg (1.01 mmol) of 8-cyano-1-cyclopropyl-7-((1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 1.03 ml (10.1 mmol) of ethyl propiolate are heated at 120° C. in 7.5 ml of methylglycol for 1 hour. The reaction solution is concentrated in vacuo and the residue is stirred with water and filtered off with suction. The resulting crude product is recrystallized from ethanol.

Workup

  1. concentrationThe reaction solution is concentrated in vacuo
  2. filtrationfiltered off with suction
  3. customThe resulting crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-abce25db9aa1409798e5e591ffb2ab9f
Source dataset
uspto-grants-2001_08
Patent number
US06278013B1

Reaction notes

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