Triethylamine → 7-(3-Azabicyclo[3.1.0]hex-3-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 373699Notes

Reaction equation

HRID 373699 reaction equation
[CH:1]12[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17](F)[CH:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[CH2:9][CH2:8]1.C(N(CC)CC)C>CS(C)=O>[CH:1]12[CH2:6][CH:5]1[CH2:4][N:3]([C:17]1[CH:18]=[C:19]3[C:14]([C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11][N:10]3[CH:7]3[CH2:9][CH2:8]3)=[CH:15][C:16]=1[F:21])[CH2:2]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 131505233-Azabicyclo(3.1.0)hexane

Product 1

HCID 157134447-(3-Azabicyclo[3.1.0]hex-3-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of the hydrochloride salt of 3-azabicyclo-[3.1.0]hexane (157 mg, 1.31 mmol), (prepared in a manner similar to that described in U.S. Pat. No. 4,183,857) in dimethylsulfoxide (13 ml) was treated with 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (348 mg, 1.31 mmol) and triethylamine (0.58 ml, 3.9 mmol) and heated for 18 hours. Filtration of the reaction mixture provided a white solid, which was purified by column chromatography (eluant: 1% acetic acid in chloroform, then 5% acetic acid in chloroform, then methanol) to give the title product as a white solid, melting point 290° (186 mg, 0.43 mmol, 33% yield). 1H NMR (DMSO-d6) 8.54 (s, 1H), 7.75 (d, J=14 Hz, 1H), 7.08 (d, J=9 Hz, 1H}, 3.83 (dd, J=4, 10 Hz, 2H), 3.73 (bs, 1H), 3.62 (bd, J=10 Hz, 2H), 1.77 (m, 2H), 1.30 (d, J=6 Hz, 2H), 1.14 (bs, 2H), 0.77 (m, 1H), 0.30 (m, 1H).

Workup

  1. temperatureheated for 18 hours
  2. filtrationFiltration of the reaction mixture
  3. customprovided a white solid, which
  4. customwas purified by column chromatography (eluant

Sources & evidence

ORD record
ord-f85aa36be82d4607850b5efb2442d93f
Source dataset
uspto-grants-1992_11
Patent number
US05164402

Reaction notes

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