Triethylamine → HCID 18509158, compound

HRID 1934485Notes

Reaction equation

HRID 1934485 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[NH2:22][C:23]12[CH2:31][CH:30]1[CH2:29][CH:28]1[CH:24]2[CH2:25][NH:26][CH2:27]1.C(N(CC)CC)C>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][CH:28]3[CH:24]([C:23]4([NH2:22])[CH:30]([CH2:29]3)[CH2:31]4)[CH2:25]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 55284375HCID 55284375, compound

Product 1

HCID 18509158HCID 18509158, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (298 mg, 1.0 mmol) was added to a solution of 1-amino-4-azatricyclo[6.1.0.02,6]nonane (206 mg, 1.36 mmol) and triethylamine (418 μl, 3.0 mmol) in acetonitrile (10 ml) at room temperature, and the mixture was heated under reflux for 16 hours. After cooling to room temperature, the acetonitrile was evaporated. To the residue was added an aqueous hydrochloric acid solution, followed by washing with chloroform. The aqueous layer was made alkaline with an aqueous sodium hydroxide solution and washed with chloroform. The aqueous layer was adjusted to pH 7.5 with an aqueous hydrochloric acid solution and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was recrystallized from ethanol. Recrystallization from 2-propanol gave 21 mg of the title compound as yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customthe acetonitrile was evaporated
  4. additionTo the residue was added an aqueous hydrochloric acid solution
  5. washby washing with chloroform
  6. washwashed with chloroform
  7. extractionextracted with chloroform
  8. dry with materialThe extract was dried over anhydrous sodium sulfate
  9. customthe solvent was removed by evaporation
  10. customThe residue was recrystallized from ethanol
  11. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-ab1e885e284a46e29f6c79a380315cd7
Source dataset
uspto-grants-2002_05
Patent number
US06384050B1

Reaction notes

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