1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 70419253, compound

HRID 580597Notes

Reaction equation

HRID 580597 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].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:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]3[CH:12]3[CH2:14][CH2:13]3)=[CH:4][C:3]=2[F:19])[CH2:29]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 483180Fluoroquinolonic acidHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidine

Product 1

HCID 70419253HCID 70419253, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.7 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.62 g), DBU (0.43 g) and anhydrous acetonitrile (30 ml) was refluxed for 52 hours. After cooling, the resulting precipitate was collected by filtration, washed with chilled acetonitrile and this was added to concentrated hydrochloric acid-methanol (1:1, 5 ml) and stirred for 40 minutes at elevated temperature. The reacting mixture was collected by filtration, washed with chilled water sufficiently and recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:3) to give the title compound (0.076 g) as pale yellow prisms, mp 268°-270° C. (decompd.).

Workup

  1. temperaturewas refluxed for 52 hours
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with chilled acetonitrile
  5. additionthis was added to concentrated hydrochloric acid-methanol (1:1, 5 ml)
  6. filtrationThe reacting mixture was collected by filtration
  7. washwashed with chilled water sufficiently
  8. customrecrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:3)

Sources & evidence

ORD record
ord-3111a90069ed46b59db7c37d3e6d21bd
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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