Acetic Acid → HCID 15136238, compound

HRID 2051195Notes

Reaction equation

HRID 2051195 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C1C[CH2:30][N:29]2[C:24](=[N:25][CH2:26][CH2:27][CH2:28]2)CC1.[C:32](O)(=O)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:25]4[CH2:26][C:27](=[CH2:32])[CH:28]([NH:29][CH3:30])[CH2:24]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 15136238HCID 15136238, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 350 mg (1.24 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (II-1), 424 mg (2.48 mmol) of 3-methylamino-4-methylene-1-pyrrolidine dihydrochloride, and 754 mg of DBU in 15 ml of acetonitrile is refluxed for 2 hours. After cooling, the reaction mixture is neutralized with acetic acid. The resulting crystals are collected by filtration, washed with acetonitrile, and dried to give 368 mg (Yield: 82%) of the objective compound (I-5). mp. 239°-243° C.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting crystals are collected by filtration
  3. washwashed with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-fd2f971d18a2415a86a623f12b202dd4
Source dataset
uspto-grants-1991_05
Patent number
US05017581

Reaction notes

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