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

HRID 1651385Notes

Reaction equation

HRID 1651385 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.C(N[CH:28]1[CH2:31][N:30](C)[CH2:29]1)(=O)C.[CH2:33]([N:35]([CH2:38]C)CC)[CH3:34].CS(C)=[O:42]>O>[C:33]([NH:35][CH2:38][CH:28]1[CH2:29][N:30]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:16])[CH2:31]1)(=[O:42])[CH3:34]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 23051779HCID 23051779, compound

Product 1

HCID 15615457Ethyl 7-[3-[(acetylamino)methyl]-1-azetidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.0 g (3.2 mmoles) of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 1.05 g (6.4 mmoles) of 3-acetamido-methylazetidine hydrochloride, 1.6 g (16 mmoles) of triethylamine and 20 ml of DMSO is heated to 80° C. for 4 hours. It is allowed to cool, poured onto a mixture of ice and water giving a precipitate which is filtered and washed with water. The solid is dried under vacuum yielding 0.93 g (69%) of ethyl 7-(3-acetamidomethyl-1-azetidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate melting at 170°-190° C.

Workup

  1. temperatureto cool
  2. filtrationis filtered
  3. washwashed with water
  4. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-73d8eb9b9a6e4e06aa11053c37f2577c
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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