Triethylamine → HCID 19792691, compound

HRID 1655545Notes

Reaction equation

HRID 1655545 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.Cl.[F:26][C:27]([F:38])([O:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1)[CH2:28][F:29].C(N(CC)CC)C.[OH-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([NH:37][C:34]3[CH:35]=[CH:36][C:31]([O:30][C:27]([F:26])([F:38])[CH2:28][F:29])=[CH:32][CH:33]=3)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[N:5]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 133700182-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)propanoyl chlorideHCID 197927024-(1,1,2-Trifluoroethoxy)aniline hydrochloride

Product 1

HCID 19792691HCID 19792691, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5.8 mmol of 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propanoyl chloride (previously prepared from 2.0 g, 5.8 mmol, of the corresponding acid) in 15 ml of acetonitrile was added to a mixture of 1.32 g (5.8 mmol) of 4-(1,1,2-trifluoroethoxy)benzeneamine hydrochloride (contaminated with approximately 20 percent of 4-(1,2-difluoroethenyloxy)benzeneamine), 1.47 g (14.5 mmol) of triethylamine and 15 ml of acetonitrile. The mixture was stirred at reflux for 2.5 hours, poured over ice and made basic with dilute aqueous sodium hydroxide. The resulting precipitate was filtered and dried (2.9 g, 97 percent of theoretical) and then recrystallized from methylcyclohexane. This gave the desired product (contaminated with approximately 20 percent of 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(1,2-difluoroethenyloxy)phenyl)propanamide) as a solid, m.p. 137°-140° C. (Compound 40)

Workup

  1. temperatureat reflux for 2.5 hours
  2. additionpoured over ice
  3. filtrationThe resulting precipitate was filtered
  4. customdried (2.9 g, 97 percent of theoretical)
  5. customrecrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-6ab33cb1dcb64407b41d93114c30fe82
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

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