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 430586Notes

Reaction equation

HRID 430586 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-39c15d8e38804487b3992c84140f3bc5
Source dataset
uspto-grants-2001_11
Patent number
US06323213B1

Reaction notes

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