Pyridine → HCID 14839388, compound

HRID 248506Notes

Reaction equation

HRID 248506 reaction equation
[CH3:1][CH:2]([O:4][CH2:5][CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1)[CH3:3].[CH2:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([F:25])=[C:21](F)[CH:22]=2)[C:17](=[O:26])[C:16]([C:27]([OH:29])=[O:28])=[CH:15]1)[CH3:13].N1C=CC=CC=1>CCOCC>[CH2:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([F:25])=[C:21]([N:10]3[CH2:9][CH2:8][NH:7][CH:6]([CH2:5][O:4][CH:2]([CH3:1])[CH3:3])[CH2:11]3)[CH:22]=2)[C:17](=[O:26])[C:16]([C:27]([OH:29])=[O:28])=[CH:15]1)[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635422-{[(Propan-2-yl)oxy]methyl}piperazine

Product 1

HCID 14839388HCID 14839388, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2 g of 2-[(1-methylethoxy)methyl]piperazine, 1.27 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 5 ml of pyridine was heated at 80° C. for 3 hours, then evaporated in vacuo. The residue was reevaporated three times from toluene, giving a gum. Ether was added to the gum which solidified. The solid was triturated with ether containing methanol and then dried giving 2.1 g of solid. A 1 g portion was purified by chromatography, giving 650 mg of the desired product, mp 144°-146° C.

Workup

  1. customevaporated in vacuo
  2. customThe residue was reevaporated three times from toluene
  3. customgiving a gum
  4. customThe solid was triturated with ether
  5. additioncontaining methanol
  6. customdried

Sources & evidence

ORD record
ord-9dac272b2a7743059d996daba7a7bb51
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

Loading…