Dimethyl Sulfoxide → 1-Cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1651383Notes

Reaction equation

HRID 1651383 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[OH:21][CH:22]1[CH2:25][NH:24][CH2:23]1.C(N(CC)CC)C.CS(C)=O>O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:24]4[CH2:25][CH:22]([OH:21])[CH2:23]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15142903-Hydroxyazetidine

Product 1

HCID 104496511-Cyclopropyl-6,8-difluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.9 g (3.2 mmoles) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.7 g (6.4 mmoles) of 3-hydroxyazetidine, 1.6 g (16.0 mmoles) of triethylamine and 15 ml of DMSO is heated to 80° C. for 4 hours. It is allowed to cool, added to a mixture of ice and water, and adjusted to pH 5 giving a precipitate which is filtered and washed with water. The solid is dried under vacuum to yield 0.86 g (80%) of 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at 286°-288° C. Spectroscopic data are identical to those of method C.

Workup

  1. temperatureto cool
  2. customgiving a precipitate which
  3. filtrationis filtered
  4. washwashed with water
  5. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-22f44a50f42f4b6089b6efe2fbe6cf5e
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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