HCID 15283247, compound → 7,9-Difluoro-1-methyl-8-(2-methylamino-8-azabicyclo[4.3.0]non-3-en-8-yl)-5-oxo-5H-thiazolo[3.2-a]quinoline-4-carboxylic acid

HRID 1599996Notes

Reaction equation

HRID 1599996 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]1[C:14]([CH3:17])=[CH:15][S:16][C:7]1=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].[CH3:22][NH:23][CH:24]1[CH:32]=[CH:31][CH2:30][CH:29]2[CH:25]1[CH2:26][NH:27][CH2:28]2>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:27]1[CH2:26][CH:25]3[CH:29]([CH2:30][CH:31]=[CH:32][CH:24]3[NH:23][CH3:22])[CH2:28]1)[N:8]1[C:14]([CH3:17])=[CH:15][S:16][C:7]1=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21]

Participants

4

Reactant 2

HCID 15283247HCID 15283247, compoundHCID 153420027,8,9-trifluoro-1-methyl-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid

Product 1

HCID 153420037,9-Difluoro-1-methyl-8-(2-methylamino-8-azabicyclo[4.3.0]non-3-en-8-yl)-5-oxo-5H-thiazolo[3.2-a]quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

100 mg (0.318 mmol) of 7,8,9-trifluoro-1-methyl-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid are heated at 80° C. under argon for 2 hours with 97 mg (0.64 mmol) of 2-methylamino-8-azabicyclo[4.3.0]-non-3-ene in 3 ml of DMSO. The mixture is concentrated in a high vacuum, the residue is recrystallized from ethanol and the product is dried.

Workup

  1. concentrationThe mixture is concentrated in a high vacuum
  2. customthe residue is recrystallized from ethanol
  3. customthe product is dried

Sources & evidence

ORD record
ord-35016ce939bd4246a83c0c352e4e0cd6
Source dataset
uspto-grants-1998_04
Patent number
US05744478

Reaction notes

Loading…