Triethylamine → HCID 14774121, compound

HRID 1081425Notes

Reaction equation

HRID 1081425 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:16])[C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C(OC([NH:28][CH2:29][C:30]1([CH3:35])[CH2:34][CH2:33][NH:32][CH2:31]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:28][CH2:29][C:30]1([CH3:35])[CH2:34][CH2:33][N:32]([C:11]2[CH:12]=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([CH3:16])[C:10]=2[F:15])[CH2:31]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146512541-Cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15129218tert-Butyl [(3-methylpyrrolidin-3-yl)methyl]carbamate

Product 1

HCID 14774121HCID 14774121, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.61 g (2.18 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.56 g (2.61 mmol) of 3-[(t-butoxycarbonyl)aminomethyl]-3-methylpyrrolidine, 0.66 g (6.54 mmol) of triethylamine, and 25 mL of acetonitrile was refluxed for 6 hours, then stirred overnight at room temperature. The precipitate was collected by filtration and washed with acetonitrile and ether. The crude product was suspended in 20 mL of 6N hydrochloric acid and 20 mL of glacial acetic acid and was stirred at room temperature for 3 hours. The solution was concentrated and the residue was triturated with ether. The solid was removed by filtration, washed with ether, and dried to give 0.61 g of the title compound as the hydrochloride, mp 250°-252° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with acetonitrile and ether
  4. stirring20 mL of glacial acetic acid and was stirred at room temperature for 3 hours
  5. concentrationThe solution was concentrated
  6. customthe residue was triturated with ether
  7. customThe solid was removed by filtration
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-d23f5e59a2d942a0b2a1a14dc993dfdc
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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