Triethylamine → HCID 67598404, compound

HRID 1415967Notes

Reaction equation

HRID 1415967 reaction equation
N[C:2]1([F:26])[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:21])=[C:16](F)[C:17]=3[Cl:19])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]2)=[CH:4][CH2:3]1.C(OC([N:34]1[CH2:41][CH:40]2[CH:36]([CH2:37][NH:38][CH2:39]2)[CH2:35]1)=O)(C)(C)C.C([N:44](CC)CC)C>C(#N)C>[ClH:19].[NH2:44][C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:21])=[C:16]([N:34]4[CH2:41][CH:40]5[CH:36]([CH2:37][NH:38][CH2:39]5)[CH2:35]4)[C:17]=3[Cl:19])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]2)[C:6]([F:8])=[CH:7][C:2]=1[F:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 67598478HCID 67598478, compound

Product 1

HCID 67598404HCID 67598404, compoundYield 181%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

In 3 ml of acetonitrile were dissolved 100 mg of 1-(4-amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 104 mg of 3-t-butoxycarbonyl-3,7-diazabicyclo[3.3.0]octane, and 150 mg of triethylamine. The solution was stirred at 80° C. for 3 hours. The solvent was distilled off in vacua. The residue was extracted with 30 ml of chloroform. The organic layer was washed with 20 ml of 3% citric acid aqueous solution, dried, and then distilled. The residue was dissolved in 20 ml of dichloromethane, combined with 5 ml of 4N hydrochloric acid/dioxane, and stirred at room temperature for 2 hours. The solvent was distilled off in vacua. The residue was solidified with isopropyl ether and collected by filtration to give 120 mg of the title compound as a pale yellow powder.

Workup

  1. distillationThe solvent was distilled off in vacua
  2. extractionThe residue was extracted with 30 ml of chloroform
  3. washThe organic layer was washed with 20 ml of 3% citric acid aqueous solution
  4. customdried
  5. distillationdistilled
  6. dissolutionThe residue was dissolved in 20 ml of dichloromethane
  7. stirringstirred at room temperature for 2 hours
  8. distillationThe solvent was distilled off in vacua
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-da9233ca3c35409b9d2b780a0e73bcb5
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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