1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 13933106, compound

HRID 580580Notes

Reaction equation

HRID 580580 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].[CH2:21]([NH:23][CH2:24][CH:25]1[CH:29]([CH3:30])[CH2:28][NH:27][CH2:26]1)[CH3:22].C1CCN2C(=NCCC2)CC1>C(#N)C>[Cl:1][C:2]1[C:3]([N:27]2[CH2:28][CH:29]([CH3:30])[CH:25]([CH2:24][NH:23][CH2:21][CH3:22])[CH2:26]2)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19853374HCID 19853374, compound

Product 1

HCID 13933106HCID 13933106, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-ethylaminomethyl-4-methylpyrrolidine (0.36 g) and DBU (0.25 g) was refluxed for 2 hours and allowed to stand overnight at room temperature. The resulting precipitate was collected by filtration, washed with acetonitrile and ether successively and recrystallized from chloroform-methanol-concentrated aqueous ammonia to give the title compound (0.56 g) as pale yellow powder, mp 254°-257° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with acetonitrile and ether successively
  4. customrecrystallized from chloroform-methanol-concentrated aqueous ammonia

Sources & evidence

ORD record
ord-c04f034564314df7907bbae8b7ff7b3d
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

Loading…