Triethylamine → HCID 3025933, compound

HRID 1081418Notes

Reaction equation

HRID 1081418 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.C(OC([NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:29][CH:30]1[CH2:34][CH2:33][N:32]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([CH3:17])[C:10]=2[F:16])[CH2:31]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 3025933HCID 3025933, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.00 g (3.36 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.63 g (3.38 mmol) of 3-(t-butoxycarbonyl)aminopyrrolidine, 1.00 g (9.91 mmol) of triethylamine, and 35 mL of acetonitrile was refluxed for 5 hours, then stirred at room temperature overnight. The precipitate was removed by filtration and washed with acetonitrile and ether. The crude product was suspended in 20 mL of 6M hydrochloric acid and 20 mL of glacial acetic acid and was heated at 60° C. for 2 hours. The solution was concentrated to an oil which was triturated with isopropanol. The solid was collected by filtration and washed with ether to give 1.04 g of the title compound as the hydrochloride salt, mp>300° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe precipitate was removed by filtration
  3. washwashed with acetonitrile and ether
  4. temperature20 mL of glacial acetic acid and was heated at 60° C. for 2 hours
  5. concentrationThe solution was concentrated to an oil which
  6. customwas triturated with isopropanol
  7. filtrationThe solid was collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-b536323649ee4010be0b66f29636ddc2
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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