Dimethyl Sulfoxide → Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1651380Notes

Reaction equation

HRID 1651380 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]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[OH:24][CH:25]1[CH2:28][NH:27][CH2:26]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:27]4[CH2:28][CH:25]([OH:24])[CH2:26]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 15615453Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.22 g (3.92 mmoles) of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 0.86 g (7.85 mmoles) of 3hydroxyazetidine hydrochloride, 2 g (19.8 mmoles) of triethylamine and 20 ml of dimethyl sulphoxide (DMSO) is heated for 4 hours at 80° C. The solution is allowed to cool and is added to a mixture of ice and water, giving a precipitate which is filtered and washed with water. The solid is dried under vacuum yielding 1.40 g (97%) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate melting at 260°-270° 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-8bed150003b24649bfc0e5f7e8aa1928
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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