Triethylamine → HCID 17782772, compound

HRID 369308Notes

Reaction equation

HRID 369308 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26].[NH2:27][CH:28]1[CH2:32][CH2:31][N:30](CC2C=CC=CC=2)[CH2:29]1.C(N(CC)CC)C>N1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH:28]4[CH2:32][CH2:31][NH:30][CH2:29]4)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27566131-Benzyl-3-aminopyrrolidineHCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 17782772HCID 17782772, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (200 mg), 3-amino-1-benzylpyrrolidine (97 mg) and triethylamine (160 mg) were added to pyridine (600 mg), and the mixture was stirred for 26 hours at room temperature and f or 15 hours at 60° C. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Acetic acid (2 ml) and 10% palladium-carbon (25 mg) were added to the resultant residue to conduct hydrogenation for 20 hours at 45° C. and for 21 hours at room temperature. After the catalyst was separated by filtration and washed with acetic acid, the filtrate and washings were concentrated under reduced pressure. A process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Ethanol (2 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (115 mg) as a pale brown powder.

Workup

  1. customf or 15 hours
  2. customat 60° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. concentrationA process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure
  5. additionAcetic acid (2 ml) and 10% palladium-carbon (25 mg) were added to the resultant residue
  6. customfor 20 hours
  7. customat 45° C.
  8. waitfor 21 hours at room temperature
  9. customAfter the catalyst was separated by filtration
  10. washwashed with acetic acid
  11. concentrationthe filtrate and washings were concentrated under reduced pressure
  12. concentrationA process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure
  13. additionEthanol (2 ml) was added to the resultant residue, and deposits
  14. filtrationwere collected by filtration
  15. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-41a55283102743f9a084ffa0ecd7ea66
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

Loading…