Triethylamine → HCID 131717097, compound

HRID 466769Notes

Reaction equation

HRID 466769 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C>C(#N)C>[ClH:1].[Cl:1][C:2]1[C:3]([N:23]2[CH2:24][CH2:25][C@@H:27]([C:11]([CH3:6])([NH:10][CH3:9])[CH3:2])[CH2:26]2)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 131717097HCID 131717097, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.42 g (1.40 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.27 g (1.90 mmol) of (3R)-(1'-methyl-1'-methylaminoethyl)pyrrolidine (11a), 0.43 g (4.3 mmol) of triethylamine and 50 mL of acetonitrile was heated at reflux for 32 hours. The reaction was concentrated in vacuo and the residue was suspended in water. The pH was adjusted to 12.0 and the solution was filtered through a fiber glass pad to clarify. The filtrate was acidified to pH 2.0 with 6.0M hydrochloric acid, filtered, and the filtrate lyophilized. The residue was suspended in 10 mL of 12.0M hydrochloric acid and filtered. The filtrate was concentrated in vacuo and the residue was removed by filtration, washed with 2-propanol, ether, and dried in vacuo to give 0.22 g of the title compound, mp 270°-273° C.

Workup

  1. temperatureat reflux for 32 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. filtrationthe solution was filtered through a fiber glass pad
  4. filtrationfiltered
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was removed by filtration
  8. washwashed with 2-propanol, ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b7963a16c5f04ca2be48c5bcc44fd8a2
Source dataset
uspto-grants-1992_10
Patent number
US05157128

Reaction notes

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