Triethylamine → HCID 14819729, compound

HRID 329897Notes

Reaction equation

HRID 329897 reaction equation
Br[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([N:13]3[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]3)=[C:8]([F:12])[CH:9]=2)[NH:4][C:3]1=[O:23].C(N(CC)CC)C>O1CCCC1.O>[F:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N:13]1[C:17](=[O:18])[N:16]([CH:19]([F:20])[F:21])[C:15]([CH3:22])=[N:14]1)[NH:4][C:3](=[O:23])[CH:2]=[CH:11]2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 14819728HCID 14819728, compound

Product 1

HCID 14819729HCID 14819729, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.0 g (0.018 mole) of 1-[3-bromo-6-fluoro-3,4-dihydroquinolin-2(1H)-one-7-yl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one in 60 mL of tetrahydrofuran was stirred, and 4.0 g (0.040 mole) of triethylamine was added. Upon completion of addition the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was concentrated under reduced pressure to give a residual solid. The solid was slurried in water and collected by filtration. The dried solid was slurried in 100 mL of hot ethyl acetate. The mixture was cooled, and the solid was collected by filtration to yield 3.6 g of 1-[6-fluoroquinolin-2(1H)-one-7-yl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one; m.p. 215°-217° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a residual solid
  4. filtrationcollected by filtration
  5. temperatureThe mixture was cooled
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-d6591b16be054ebf923cbe71cbc8c02e
Source dataset
uspto-grants-1990_01
Patent number
US04894084

Reaction notes

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