1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580589Notes

Reaction equation

HRID 580589 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH3:13])[CH:9]=[C:8]([C:14]([OH:16])=[O:15])[C:7]2=[O:17].C(OC([NH:27][C@H:28]1[C@@H:32]([CH3:33])[CH2:31][NH:30][CH2:29]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:27][C@H:28]1[C@@H:32]([CH3:33])[CH2:31][N:30]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:17])[C:8]([C:14]([OH:16])=[O:15])=[CH:9][N:10]3[CH2:12][CH3:13])=[CH:5][C:4]=2[F:18])[CH2:29]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidineHCID 127708958-Chloro-1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 704197137-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 31.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-chloro-1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.25 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.21 g), DBU (0.15 g) and anhydrous acetonitrile (4 ml) was refluxed for 2.5 hours. Then, the reacting mixture was treated as described in example 22 to give the title compound (0.1 g) as white powder, mp 222°-224° C. (decompd.).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. additionThen, the reacting mixture was treated

Sources & evidence

ORD record
ord-b6c87eb13d2a4694ae17c2898b584fb1
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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