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Hydrochloric Acid → 2-(4-((5-Chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

HRID 1655544
Notes
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Reaction equation

HRID 1655544 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15](Cl)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.Cl.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([NH:30][C:29]3[CH:31]=[CH:32][C:26]([O:25][C:24]([F:23])([F:33])[F:34])=[CH:27][CH:28]=3)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27810604-(trifluoromethoxy)aniline HydrochlorideHCID 197926722-[4-(5-Chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride

Product 1

HCID 197926782-(4-((5-Chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamideYield 15%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.8 mmol of 2-(4-((5-chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)propanoyl chloride (previously prepared from the corresponding acid) in 15 ml of methylene chloride was added, under N2, to an ice-cooled mixture of 1.03 g (4.8 mmol) of 4-(trifluoromethoxy)aniline hydrochloride, 0.95 g (12 mmol) of pyridine and 25 ml of methylene chloride. The resulting mixture was stirred at ambient temperature overnight and then poured into dilute aqueous HCl. The aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were washed twice with saturated aqueous sodium bicarbonate, treated with charcoal and MgSO4 and filtered. The filtrates were evaporated to dryness and the residue recrystallized from methylcyclohexane to give 0.34 g of the above-named product as colorless crystals, m.p. 92°-93.5° C. (Compound 37)

Workup

  1. temperaturecooled
  2. customThe aqueous layer was separated
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed twice with saturated aqueous sodium bicarbonate
  5. additiontreated with charcoal and MgSO4
  6. filtrationfiltered
  7. customThe filtrates were evaporated to dryness
  8. customthe residue recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-d765d128b5754ab9a36f3c5abf389291
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05250690

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes