tert-butyl N-(pyrrolidin-3-yl)carbamate → 7-[3-[[(1,1Dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid

HRID 364054Notes

Reaction equation

HRID 364054 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([NH:14][CH3:15])[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19].[NH:20]1[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21]1>C(#N)C>[CH3:30][C:28]([CH3:31])([O:27][C:26]([NH:25][CH:22]1[CH2:23][CH2:24][N:20]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:19])[C:6]([C:16]([OH:18])=[O:17])=[CH:7][N:8]3[NH:14][CH3:15])=[CH:3][C:2]=2[F:1])[CH2:21]1)=[O:32])[CH3:29]

Participants

4

Reactant 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 135580371-Methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 705150537-[3-[[(1,1Dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acidYield 57.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.00 g (3.68 mmol) of 6,7,8-trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid in 10 ml of acetonitrile was added 0.56 g (1.0 equivalent) of 1,8-diazobicyclo-[5,4,0]undec-7-ene and 0.68 g of 1,1-dimethylethyl 3-pyrrolidinylcarbamate. The mixture was refluxed for one hour and stirred at room temperature overnight. The solids were filtered and washed with ether to give 0.92 g of 7-[3-[[(1,1dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid. A portion of this material (0.38 g) was treated with 10 ml of trifluoroacetic acid for 2 hours and was concentrated. The residue was taken up in aqueous sodium hydroxide to pH 12.5 and then treated with hydrochloric acid to pH 7.0. The solids were filtered to give 0.24 g of 7-(3-amino-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, mp 210°-211° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe solids were filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-597dd3106fde4a2189a52777bbd0c6a2
Source dataset
uspto-grants-1986_08
Patent number
US04604401

Reaction notes

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