Dimethyl Sulfoxide → HCID 73530185, compound

HRID 1197493Notes

Reaction equation

HRID 1197493 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[OH:22][N:23]=[C:24]1[CH2:28][CH2:27][NH:26][CH2:25]1.FC(F)(F)C([O-])=O.C(N(CC)CC)C.CS(C)=O>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][CH2:28][C:24](=[N:23][OH:22])[CH2:25]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 86747461HCID 86747461, compound

Product 1

HCID 73530185HCID 73530185, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

298 mg of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3 -carboxylic acid 535 mg of 3-hydroxyiminopyrrolidine-trifluoroacetate and 404 mg of triethylamine were reacted at 80° C. for 15 hours using as a solvent a mixture of 5 ml of dimethyl sulfoxide and 15 ml of acetonitrile. After cooling, the precipitate thereby formed was collected by filtration and recrystallized from a mixture of 10 ml of dimethyl sulfoxide and 15 ml of isopropanol to give 210 mg of the desired product as yellow powder.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate thereby formed
  3. filtrationwas collected by filtration
  4. customrecrystallized from a mixture of 10 ml of dimethyl sulfoxide and 15 ml of isopropanol

Sources & evidence

ORD record
ord-5b2748984d244bdfb419124a6eeef712
Source dataset
uspto-grants-1994_01
Patent number
US05276041

Reaction notes

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