Triethylamine → HCID 14774121, compound

HRID 2073847Notes

Reaction equation

HRID 2073847 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 six hours, then stirred overnight at room temperature. The precipitate was filtered 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 three hours. The solution was concentrated and the residue was triturated with ether. The solid was filtered and washed with ether to give 0.61 g of the title compound as the hydrochloride, mp 250°-252° C.

Workup

  1. temperaturewas refluxed for six hours
  2. filtrationThe precipitate was filtered
  3. washwashed with acetonitrile and ether
  4. stirring20 ml of glacial acetic acid and was stirred at room temperature for three hours
  5. concentrationThe solution was concentrated
  6. customthe residue was triturated with ether
  7. filtrationThe solid was filtered
  8. washwashed with ether

Sources & evidence

ORD record
ord-38453386273c4350bc7986eec2968b37
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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