Triethylamine → 7-[3-(Aminomethyl)-3-methyl-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid

HRID 1081420Notes

Reaction equation

HRID 1081420 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.[CH3:22][C:23]1([CH2:28][NH2:29])[CH2:27][CH2:26][NH:25][CH2:24]1.C(N(CC)CC)C>C(#N)C>[NH2:29][CH2:28][C:23]1([CH3:22])[CH2:27][CH2:26][N:25]([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])[CH2:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14235023(3-Methylpyrrolidin-3-YL)methanamineHCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 147741087-[3-(Aminomethyl)-3-methyl-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.60 g (2.02 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.28 g (2.45 mmol) of 3-methyl-3-pyrrolidinemethanamine, 0.61 g (6.06 mmol) of triethylamine, and 20 mL of acetonitrile was refluxed for 4 hours, then stirred at room temperature overnight. The precipitate was removed by filtration, washed with ether, and dried in vacuo to give 0.61 g of the title compound, mp 182°-184° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe precipitate was removed by filtration
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d99e43ed26e6485ba6232221a88c5387
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

Loading…